Sneaky wizard to fill rogue role

[Hiro Quester]

I was going to play a celestial barbarian/fighter/cleric as tank and backup healer in our up-coming campaign. Party is monk, ranger and divine soul sorcerer (who is a doctor). But another player just joined, playing a celestial vengence paladin. So we have lots of damage-dealers, and our main arcanist is also our healer.

So perhaps we need a wizard. Particularly one who can also fill in as stealthy scout, lock-opener, trapsmith, etc.

Perhaps a rogue/wizard multiclass (e.g. abjurer/arcane trickster), if it’s fun to play. (We are not necessarily a fully optimized party.)

But I’m thinking it must be possible to make a wizard with decent dexterity, and proficiency in the right skills, who might be able to fill in that role as well. Maybe an illusionist might be fun and thematically relevant. Or a bladesinger perhaps.

(I’m playing a bard in another campaign, so I don’t want to just make a sneaky bard.)

Suggestions or tips would be welcome, please.

[RSP]

I was going to play a celestial barbarian/fighter/cleric as tank and backup healer in our up-coming campaign. Party is monk, ranger and divine soul sorcerer (who is a doctor). But another player just joined, playing a celestial vengence paladin. So we have lots of damage-dealers, and our main arcanist is also our healer.

So perhaps we need a wizard. Particularly one who can also fill in as stealthy scout, lock-opener, trapsmith, etc.

Perhaps a rogue/wizard multiclass (e.g. abjurer/arcane trickster), if it’s fun to play. (We are not necessarily a fully optimized party.)

But I’m thinking it must be possible to make a wizard with decent dexterity, and proficiency in the right skills, who might be able to fill in that role as well. Maybe an illusionist might be fun and thematically relevant. Or a bladesinger perhaps.

(I’m playing a bard in another campaign, so I don’t want to just make a sneaky bard.)

Suggestions or tips would be welcome, please.

Bladesinger /AT goes together quite well and you can choose plenty of spells that augment that to a magic rogue tank roll.

However, I’d suggest you can equally accomplish it going straight Wizard. Just prioritize Dex>Con>Int and build your spell list for what you’d like to accomplish and you should be fine (particularly in a group not to using on optimizing, but Wizards hold up fairly well - particularly BS - if built for the role). Grab Thieves Tools and Stealth through background and you should be fine.

[Psyren]

You can definitely be sneaky as just a wizard, but I'd probably go with a multiclass given your group as well. I'd probably start as wizard given that you get more stuff from grabbing rogue after 1st level than the reverse.

[Nidgit]

As long as you pick up Stealth and Thieves' Tools from a background, you should be fine going mainly Wizard with maybe a 2-3 level dip in Rogue. I'd give your race a good amount of thought though- something like Firbolg, Goblin, Halfling, or Deep Gnome could add a lot of sneaky versatility.

You could also just go with a Druid or Trickery Cleric to split healing duties and still have some good stealth options.

[Hiro Quester]

I really not averse to multiclassing (quite the opposite; I have never played a straight-classed character).

Starting as Rogue1 for more skill proficiencies (from a bigger and better list for rogue role) and expertise seems prudent, no? Then wizard all the way?

For this party a battlefield control/buffer type wizard might be good. Perhaps that’s a clockwork soul sorcerer, even?

[kazaryu]

You can definitely be sneaky as just a wizard, but I'd probably go with a multiclass given your group as well. I'd probably start as wizard given that you get more stuff from grabbing rogue after 1st level than the reverse.

what? going wizard first you lose all the rogue weapon proficiencies and 1 skill proficiency. obviously if you were to go bladesinger you could eventually replace the weapon proficiency..or close enough at least. going rogue first...all you lose out on wizard is starting equipment. which could be annoying if you're starting out at> lvl 1 and your DM is a ****. but like...the only thing that wizard gives you is wis save proficiency. which, don't get me wrong, is good. but so is dex save proficiency so...

i guess im just confused by what you mean. for a character trying to fill the role of a rogue, i feel like losing out on that skill proficiency is pretty big.


As long as you pick up Stealth and Thieves' Tools from a background, you should be fine going mainly Wizard with maybe a 2-3 level dip in Rogue. I'd give your race a good amount of thought though- something like Firbolg, Goblin, Halfling, or Deep Gnome could add a lot of sneaky versatility.

You could also just go with a Druid or Trickery Cleric to split healing duties and still have some good stealth options.

rogues always come with thieves tool proficiencies. no need to get them elsewhere.

[LudicSavant]

Arcana is one of the best anti-trap skills in the game (since it can detect, locate, *and* disarm *all* magical and spell traps, substituting for any skills that can normally apply. Do not forget about this rule!! It’s in the DMG section on traps!! Use it!!). A Wizard’s high Int makes them well suited to using it.

A winged familiar will get you a high passive perception out of the gate (18 or 19 because of their Keen Senses). Use Flyby to keep ‘em safe. They’re your eyes 👀

And Wizards are of course well suited to Investigation, another important dungeoneering skill (assuming your DM is using it correctly and not mistakenly using Perception for everything)

Thieves’ Tools can be picked up from your background.

The Warding Dwarf is a great race for Wizard which, among other things, gives them pseudo-expertise in anti-trap skills.

That’s just the start. Can probably say more if/when I have some time.

[Sage Tellah]

Int-base caster and skill monkey who's good with traps in a low-optimization group? Everything you're asking for screams Artificer to me. Half-wizard, half-rogue, tons of interesting utility, and I dunno how kitted out your group is for magic items but Artificer can make up for a deficiency. It's printed in Tasha's.

[Hiro Quester]

Artificer does seem a good option, too. I guess the armorer variant, with the option to make armor that has advantage on stealth and no strength requirement. Hmmm…

Still, I have an image I’m playing with, of the rogue 2 with expertise in stealth, who takes on the role of battlefield controller and buffer, but does so while lurking in the shadows, hidden.

But they have the ability to use blade song when they need to. Shadow blade seems fun to use here, too.

Or maybe a mix of arcane trickster and bladesinger, if I went deeper into rogue. But starting as rogue 2/wizard 1, probably. AT for disabling traps from a distance seems prudent.

I’m a newbie at both rogue and wizard classes though. There are a plethora of options to consider here. But the mix seems like a fun combo, since pumping dex and int seems to have a lot of synergy. Advice sincerely appreciated.

[Selion]

If you're not into optimization, two levels of rogue are everything you need to feel roguish. Light armors, weapons and thieves tools proficiencies, expertise and cunning action.
In tier 1/2 you can somewhat emulate a weaker sneak attack with booming blade, which is great if you can move/attack/disengage to proc eventually the secondary damage.
You'll be weaker than a full wizard, though (everything is weaker than a full wizard to be honest)

[Hiro Quester]

We are starting at level 3. So I think one level of rogue, then wizard 2. And take wizard to 6, before deciding whether or not I need the cunning action. The option of being a goblin for bonus action disengage or hide saves a rogue level, though.

With the rest of the party being damage dealers (paladin, monk, ranger, sorcerer), I’m thinking that taking mostly buff, debuffer and BFC spells would be best.

Which subclass would work best for BFC controller type? If I’m occasionally in the thick of it, then Bladesinger calls to me here. Especially with rogue (booming blade, attack, plus disengage). Though enchanter might be good for crowd control. Or chronurgist. Thoughts?

.

[Mastikator]

Goblins can hide as a bonus action.
The urchin background (PHb) gives thieve's tools proficiency and stealth proficiency.

You can go straight wizard as a goblin urchin. Expertise is nice but not necessary. High level wizard spells is a lot nicer. Starting at level 3, as a 3rd level wizard you'd get instant access to Invisibility, Levitation, Hold Person, Suggestion, Phantasmal Force and many other CCs, buffs and debuffs.
At level 5 I'd say look out for Slow and hypnotic pattern.

[Corran]

I really not averse to multiclassing (quite the opposite; I have never played a straight-classed character).
In case you want to try out one, goblin, pick relevant bakground for proficiencies (and feature), casting stat>DEX>else, skulker. Optionally pick a feat that will give you expertise or lucky for some extra oomph in your ability checks.

[OptimizedAC]

Goblin and Skill expert puts you on par with the rogue-class in terms of stealth, without sacrificing two spellcasting levels. You'll have to level up once to come fully online, but you'd also start with access to Invisibility, and earlier access to a lot of delightful spells (as well as the spell-slots to use them).

As opposed to going to two levels into rogue, pure wizard doesn't give armour-proficiency (but gets higher AC from spending one of its extra slots on mage armour), one fewer skill (and tool) proficiency and expertise than rogue, and no sneak attack. (You also get a couple of HP more, but lose proficiency in Wis-saves. And while you don't lock in the Wizard 4 feat, it's a half-feat you're avoiding, and you only get to choose some other feat when the pure wizard would be halfway to the next feat)

Unless your vision includes martial attacks, the crucial benefit here is that you free up your race. Some examples of what that opens up:
Earth genasi (MPMM): Pass without trace boost your stealth to incredible levels, and also buffs a rather stealth-friendly party. You'll only get it once-per day until level 5, when the ranger also have access to it. But first of all, that is enough to count. Second of all, the ranger will not have the spell-slots or spells known that you'll have after level 5, so saving them from casting it is plently useful. Third of all, the Earth walk and bonus action blade ward are both nice to have when you need them.
Wood elf: If the DM considers light to be a natural phenomenon, and the lightly obscured of darkvision to fall under Mask of the Wild, then that is the most important part of the skulker-feat
Variant human/custom lineage: If it's not, then you can just take the skulker-feat, or whatever else compliments your vision. Metamagic adept let's you Silent Spell twice in a day, for when staying undetected while casting is essential, for instance - but this is more an opportunity to note for later levels.
Lightfoot halfling: Again a PHB-race that supports stealth. While I gravitate towards the other options, it should be mentioned that as a caster you can eventually take advantage in a distinct way - summon or raise a creature larger than you, and hide behind them.

"We are starting at level 3. So I think one level of rogue, then wizard 2. And take wizard to 6, before deciding whether or not I need the cunning action."

"Still, I have an image I’m playing with, of the rogue 2 with expertise in stealth, who takes on the role of battlefield controller and buffer, but does so while lurking in the shadows, hidden."

These two visions don't jive unfortunately. With just one rogue-level, you're lurking in the shadows - until appearing from it the first round of combat. After one level in your game, with Skill expert, as a pure wizard you'll be as good in stealth and better at magic as the rogue dip - or possibly better if you put the stat-boost to dex (you don't really need to, +3 and expertise is plenty for stealth).

My main advice in this long-ass post is that: In terms of fun to play, I think starting as a full wizard delivers on your vision while also complimenting it as a caster.
Rogue 2 / Wizard 5+ opens up being extra stealthy in a distinct way, but you'll be playing for a while before you reach a level where your casting supports your core theme. And you'll always be a less powerful caster, with the diminished fun that follows from that.
Rogue 1/ Wizard x is a mistake.



Let's jump into something more specific - which school to choose? You've brought up the most relevant ones (unless you want to be a halfling who avoids notice behind their rotting zombie). While there is some variation in power-level, the difference in style is likely more significant for your choice - how do you want to skulk in the shadows?

Not just casting spells, but occasionally merging to strike deathly blows - swift and evasive? As a bladesinger, note that your primary defensive strategy is not being targeted. That makes the relevance of the AC-bonus more conditional - but potentially a godsend when stealth isn't on the table and the table is a mimic.
Tricking others with magic, while concealing your presence so they'll stay oblivious to the trick? Illusion only peaks in objective strength at level 14, but at lower levels it's still oriented towards a fun playstyle that mashes well with your concept - and with the right DM, can be just as impactful at lower levels as other schools.
Hiding from others while you manipulate their flow of time? Chronurgy boosts initative, which isn't actually stealth but somehow still makes you feel more stealthy. More relevant for your vision are it's debuff-support in its early features.
Staying out of view until a target is vulnerable, approaching to take over their mind. Enchantment is the school I personally plan to play with a similar build as soon as I can. While the other schools interact in powerful and fun ways with the stealth-build, from this schools synergy novel playstyles emerge.

All are good options, tbh.

Outside of combat, you get a distinct benefit from your stealth - throw on invisibility, get close to a non-deafened target and hypnotize them. They're now incapacitated and charmed - letting you both set up combat and non-combat shenanigans. Crucially, your invisibility is not broken, as you've cast no spell. (An illusionist can also have great fun outside combat, but hardly use their features and stay invisible). The two other subclasses are heavily combat-focused.

Also here, the enchanter shines. In combat, Hypnotic gaze becomes viable in new ways when you can also sneak or disengage. If you can somehow hide while within 5 ft of a monster (which is admittedly easier as a Halfling rogue 2/wizard 2 than as a goblin) you're pretty safe to keep them locked down. And if you're not within 5 ft of a creature, you probably don't wanna risk changing that in case the hypnosis doesn't land and you eat an opportunity attack - the goblin enchanter can skirmish around creatures reach until it takes someone out of the fight. You're combining being in the thick of it like a bladesinger, with the debuffing you also want.

Personally, when I play it, I will dip either into artificer or cleric. When stealth isn't an option, artificer doesn't only give proficiency in con-saves, shield and armour plus some nice ribbons - it's int-based Sanctuary doesn't end with Hypnotic gaze. Cleric also have some nice subclasses, armour, and nice spells even when Wis-based. Also, I'm a sucker for more cantrips. However, I wouldn't recommend such multiclassing for you, especially until after level 5. I think you'd have less fun if you didn't get expertize in stealth until level 5. I'm not sure if wearing shields fits your vision. And getting quick access to 3rd level spells is significant. But there are some Cleric subclasses that themes in on your build well enough that you could consider it after that.

[Hiro Quester]

My main advice in this long-ass post is that: In terms of fun to play, I think starting as a full wizard delivers on your vision while also complimenting it as a caster.
Rogue 2 / Wizard 5+ opens up being extra stealthy in a distinct way, but you'll be playing for a while before you reach a level where your casting supports your core theme. And you'll always be a less powerful caster, with the diminished fun that follows from that.
Rogue 1/ Wizard x is a mistake.

Please don't apologize to me for long posts. Mine are often very long, too. When the ratio of wordiness to useful information remains high, the length is justified. (Your post more than qualifies; more than many of mine). I appreciate you taking the time to be helpful.

I'm not sure I'm seeing why Rogue 1Wizard x would be a mistake, when two levels of rogue would "open up new levels of being stealthy".

Unless you just mean that a goblin wizard with urchin background can have most of this without sacrificing ing one level of spell progression? They would have two fewer proficiencies, no expertises and no sneak attack? I guess I see that. After playing a bard, I really like having expertise in a couple of key skills, though.

It seems that there are five or six skill proficiencies you would want: arcana, perception, investigation, stealth, and thieves tools, and either calligraphy (for forging documents) or a disguise kit, seem necessary for the role. Acrobatics and sleight of hand would be good, and deception or persuasion might be useful).

We are allowed to make up custom backgrounds in our game, especially if we have a creative backstory to support it. Wizard with a custom background that granted perception and investigation (like a "Little Bird" urchin, recruited as a spy by a local mage) could have the main four.

You are right that Skill Expert might be a good way to go on that base. Get Int from 17 to 18, add another useful skill, and expertise with investigation or thieves' tools.

A goblin would already have disengage and hide as bonus actions. So a goblin rogue1/wizardX seems to have a lot going for it. Two expertises, two more proficiencies and proficiency with thieves' tools, and disguise kit, a small amount of sneak attack when you are hidden and concentrating on another spell (leap out of the shadows to booming blade, then disengage as a bonus action to encourage them to move and take the secondary damage).

Perhaps you mean also that two levels in rogue grants all that, while opening up other races and backgrounds?


Speaking of other races, in our world the DM has made a custom race that might be perfect here. It's possibly a little OP, because the DM is encouraging us to try it out.

"Mohki" are a small 3ft tall cat-like race, refugees from the feywild a couple centuries ago, who are natural tinkers with proficiency in firearms (they love blowing things up!), and a good chunk of Obsessive-compulsive and ADHD (intense concentration when they are really interested in, but easily distracted by curiosities otherwise).

They have Darkvision and advantage on perception with hearing. Proficiency in perception (that becomes expertise if you also get it from background or class), and proficiency with alchemy. +2 int, +1 Dex, fey ancestry (adv against charms), double proficiency in knowledge (history) checks about magical items, alchemical objects and technology devices. They have disadvantage on deception and intimidation, though.

It's a great mix for a rogue and/or wizard, and maybe encourages an artificer dip (which I hear can be a good complement to wizard, and the stealth-enhancing armor sounds beneficial).

They are not always subtle, but love big flashy booms and surprises. I could make that work as a roguish type wizard. Seems to lend itself to warmage, perhaps. Evoker too, but I'm underwhelmed by that and its mot what th party needs.

There is some obvious roleplaying and optimization possibilities here.



Let's jump into something more specific - which school to choose?


I'm really leaning hard towards enchanter. after 10th level, being able to hit two targets with take-you-out-of-the-fight spells increases the chances of hitting at least one of your targets, and if you take two out with a hold person or hideous laughter, that's a good use of your concentration in many encounters. It makes many okay debuff spells really good. And being able to do this, and then to go up to another and hypnotize them seems worth it.

The hypnotic gaze seems a good ability. But it takes your action each round to maintain it. If you are concentrating on another valuable BFC or twinned enchantment, then this might be worth it. But it leaves you somewhat vulnerable in the middle of the fight, which also makes you a target.

You could avoid that by being invisible, but then this is taking your concentration. And then all you are doing each round is trading your actions for those of this enemy.

Hmm.. Unless you are a halfling, who can also hide behind the person you are hypnotizing with words rather than gaze. Or if you are hiding in the shadows concentrating, and use this ability to defend yourself from the person who spots you and comes to attack.

The 6th level instinctive charm to make that person attack their friend seems a good ability for that situation, too.

Enchanter is sounding like a fine subclass. Thanks.

But with the Mohki, perhaps a warmage generalist might be more their style. They typify the joke about wizards and fireballs, but I'd play this one as interested in control. I can see fun ways to fluff some control spells as cat toys, shiny distractions, etc. Enchanter would work well there too (hypnotize someone with a red laser dot on the floor by their feet that they can't resist trying to step on.)

their affinity for technology and explosions lends itself to an artillerist or armorer alchemist, too. A warmage with an armorer dip (with the infiltrator armor) might ba a cool addition to the party and further enhance the roguishness without a rogue dip. Hmmm...

I think I'm seeing some interesting way to flavor this. I'm going to build a few trial options and see how it looks.

Thanks for helping me think through this.

[LudicSavant]

I'm not sure I'm seeing why Rogue 1Wizard x would be a mistake

Wizards get a lot of sneaky utility from Wizard levels, and generally it takes a lot for it to be worth delaying their spellcasting progression. Expertise may not be worth it -- after all, there are a lot of ways to get fat skill bonuses (such as from race, feats, or spells). As well as things that are not skills, but solve the same problems.

For example, say you're level 4. You could be a Wizard 3 / Rogue 1 with Expertise in 2 skills (getting +2 to those skills) and 17 Int. Or you could be a Wizard 4 with an ASI in Skill Expert, and therefore Expertise in 1 skill (+2 to that skill) and 18 Int (+1 to all Int skills, and your spellcasting), an extra cantrip known (which can be one that helps sneaky utility), and an extra 2nd level spell slot.

Let's say you're level 5. You could be a Wizard 4 / Rogue 1, or you could be a Wizard 5 with delicious 3rd level spells. And 3 extra spell slots (2 3rd levels, and 1 more from Arcane Recovery scaling at 5). And third level rituals auto-prepared.

Let's say you're level 6. You could be a Wizard 5 / Rogue 1 for Expertise, or you could be getting another precious 3rd level slot and an Arcane Tradition feature like, say, a Bladesinger's Extra Attack, or a Diviner's Matryoshka Doll spell slots (which let you spam things like Detect Thoughts, Clairvoyance, Locate Object, See Invisibility, Borrowed Knowledge, or Mind Spike).


I'm not sure I'm seeing why Rogue 1Wizard x would be a mistake, when two levels of rogue would "open up new levels of being stealthy".
Having Expertise in stealth gives you a bonus to your stealth checks, but you still basically use stealth the same way, pre-casting it with an Action.

Having Rogue 2 makes you use Stealth in a very different way, allowing you to Hide after taking your Action in combat.

Of course, you can get much of the benefit of Rogue 2 from being a Goblin.


After playing a bard, I really like having expertise in a couple of key skills, though.

Which 2 skills would you be taking Expertise in?

[RogueJK]

Lots of good advice so far about how to make a rogueish Wizard. I agree that a Goblin with Skill Expert and no multiclassing is a better option for a Wizard than dipping Rogue.

But if you can, double-check with the Monk player to ensure they're not planning to fill the party Rogue needs. Monks, being DEX-based, are a natural Rogue substitute. Especially with stuff like Shadow Monk.

[Mastikator]

A goblin full wizard with skill expert is arguably more sneaky than a rogue dipped one. A rogue can't cast invisibility, a wizard can. Their actual stealth skill will be the same.

What you'd get out of rogue levels are things like sneak attack, rogue's cant and bonus action dash. (you already can get bonus action hide/disengage from goblin).

Arguably you could take magic initiate for the guidance cantrip and use it for out of combat stealth and thieve's tools. It's a non-trivial +1d4. However guidance is on the artificer spell list and you could be even sneakier and trappier with a dip into artificer than a dip into rogue, provided you still choose goblin. It frees up your background.
Artificers get mainly CC, buffs and debuffs. For example you probably want to have faerie fire.

[Eldariel]

Int Sanctuary is also great. As is Magic Stone. That said,on such a low level, there's no substitute for full casting; e.g. Invisibility and Enhance Ability and Misty Step are all great. For race, Mark of Shadow Elf for Pass without Trace or Goblin for Cunning Action or just Vuman/CLineage for Skill Expert. I personally played Diviner in such a role to great success: automaking or failing checks is huge.

[Hiro Quester]

I’ve built this two ways, as straight wizard3, and as artificer1/wizard 2.

I have to say that the one level of artificer brings a lot of benefits, in terms of access to spells, con saves, tool proficiencies, and medium armor and shield.

I’m playing the DM’s home brewed cat-like race, gets +2 int (to 17) +1 Dex (to 16), they are naturally curious and get engrossed in puzzles. They are also naturally chaotic and love big explosions.

They also have a natural affinity for alchemy. The community he grew up in is a major manufacturer of gunpowder and gadgets for making big explosions. He grew up playing in the lab exploding things with his father. Dm has also ruled that this race and a level in alchemist will also earn proficiency with firearms (and this small creature can use comically large firearms without penalty).

They also have dark vision, and are naturally perceptive, so proficiency in perception from class or background gets expertise. And they have advantage on perception checks involving hearing.

And for comic relief that are terrible at deception and intimidation (because they are too small and cute). Like so awful that if you try to help, you transfer your disadvantage with these.

So either way, As pure wizard or as artificer 1/ wizard X, I can play the rogue role well. I have proficiency in alchemist’s tools and thieves’ tools. And proficiency in arcana, investigation, perception, sleight of hand, and stealth.

Skill expert can get Int to 18, and expertise in perception and investigation. I’d like expertise in thieves’ tools, but I’ll have access to a knock spell (and a friend with a big hammer) to deal with doors and chests, and mage hand for when we need to set off a trap remotely.

So built as a wizard, with 16 dex, I have Ac 13, 16 with mage armor.

As artificer 1/wizard 2, though, I also have con save proficiency, which is huge for concentrating on spells (and saves on resilient feat), Ac17 from studded leather and shield (saving spell slots) and access to two more cantrips including guidance (for crucial skill checks), and also cure wounds. And proficiency in two more tools (tinkering for magical and mechanical devices, and calligraphy for forging passes and so on). And proficiency in firearms from artificer + race, too.

And I have the same number of spell slots, but one level delay in acquiring new spells. There are lots of good spells to upcast.

From a pure optimization perspective, a one level delay in getting spells and ASIs is something. But having these benefits seems okay compensation.

And from a roleplaying perspective, playing a chaotic and curious tinker, alchemist, locksmith, forger, and arcanist who loves solving puzzles and has a dangerous level of insatiable curiosity, and enjoys big explosive surprises, seems like fun.

Being a small furry cat-like wizard/artificer who likes blowing things up and who has a comically large firearm (sawn off shotgun, perhaps) also seems fun. Rocket raccoon, but less grumpy and nihilistic. Worshipping the god of trickery, who likes disrupting orderly systems and playing with them adds some fun to all this, too.

And I think playing an enchanter, who can begin to learn how to manipulate and distract people to solve problems seems a fun way to add to all this, and gives room for character growth.

I don’t get the goblin’s free hide and disengage, but I can work around that.

If I’m missing something crucial, please let me know. But we start the campaign in a week, so I need to make a commitment to the broad idea now, and get to work nailing down backstory details.

Thanks again for helping me think it all through. All your advice was very helpful.

[Eldariel]

I like Expertise in Stealth (though just Alert or Lucky is also really good - in the end I switched from Prodigy to Alert since the Expertise bonus just didn't amount to as much as Alert, which saved our collective bacons multiple times). It's just a fairly commonly rolled skill and one where failure has significant consequences. Expertise + advantage from Enhance Ability makes you very nearly infallible.

[Hiro Quester]

I would love stealth expertise. But since my character is also an alchemist 1/ wizard X, who loves solving puzzles, it makes sense for my only expertise to go to investigation.

Investigation is probably going to be one of the most common skill checks my character makes. It applies to basically all my party roles: opening locks and finding traps, searching for clues or treasure, as well as for understanding the results of experiments in combining alchemy, tinkering, and the arcane.