Advice for my Human Private Investigator Rogue

[Seerus]

Hello all,

So, I'm a fan of the cliche 40s-50s Private Investigator and want to build a character like that. Here is what I have so far, followed by some questions I have.

Human Variant Rogue

Strength, Constitution, and Charisma at 8. Dexterity, Intelligence, and Wisdom at 16

The character is a 35-40 year old man who has been a Private Investigator for 15-20. 15-20 years is also how long he has been a chain smoker, which is reflected in the low Strength and Constitution scores. His Charisma is low because he can't resist making snide comments at people even when he shouldn't, and his Dexterity is only high because he knows how to hide and is a pretty good shot, he is not acrobatic in the slightest. His high intelligence and Wisdom represent his experience as a P.I.

For skills, he has Stealth, Sleight of Hand, Investigation, History, Perception, Insight, and Survival.

His Expertise is in Perception and Investigation and his Human Variant feat is Observant, giving him passive Perception and Investigation of 22 at level 1, and reaching Passive 30 at level 17.

To represent the P.I. aspect of him, I want him to fight using the closest thing to a pistol that the game has, hand crossbows. As such, my plan for feat/ability score boosts is to get Crossbow Expert, Sharpshooter, and boost my Dexterity to 20.

My questions are as follows:

1) Given that hand crossbows have only 30 foot range until you get sharpshooter, is my Con of 8 going to get me killed because I am too close to my opponents?

2) The following feats seem useful for my build, can I get opinions on them for this build: Alert, Dungeon Delver, Skulker.

3) Which Rogue sub-class should I aim for? I am currently leaning against Arcane Trickster because I want to dual-wield crossbows eventually, but strong spell suggestions would change my mind. And I am completely split between thief and assassin right now.

4) Considering the archery boost at 1st level, action surge at 2nd level, and improved Crit at 3rd level (and sneak attack doubles on crits, I'm told), would it be a good idea to take a few levels of Fighter? And if so, what amount would be Optimal?

Thanks in advance for any help.

[iTreeby]

1) probably
2) skulker seems most in line with your concept because it makes him more perceptive
3) thief, bonus actions to manipulate clues!
4) no idea!

[Doomchild]

Taking the Observant feat at 1st level is overkill. Taking it ever is probably overkill. With expertise your passives will be 17 which is high enough to automatically notice almost all traps and clues at 1st level. And your proficiency bonus will increase faster (because it's doubled) than the DCs. I would recommend taking Crossbow Expert at 1st level to give you some kind of combat edge, because you're going to need it with negative Con. And dual wield those hand crossbows.

[Seerus]

Taking the Observant feat at 1st level is overkill. Taking it ever is probably overkill. With expertise your passives will be 17 which is high enough to automatically notice almost all traps and clues at 1st level. And your proficiency bonus will increase faster (because it's doubled) than the DCs. I would recommend taking Crossbow Expert at 1st level to give you some kind of combat edge, because you're going to need it with negative Con. And dual wield those hand crossbows.

You make a good point. But now I am wondering if I should go with Crossbow Expert, for the extra attack, or if Sharpshooter might be more worthwhile because it removes range penalties and would thus let me stay up to 120 feet away from enemies while I shoot. I haven't gotten a chance to test run anything yet, so I don't know if it is better to have more attacks and kill things fast or better to be good at keeping my distance.

[Doomchild]

You make a good point. But now I am wondering if I should go with Crossbow Expert, for the extra attack, or if Sharpshooter might be more worthwhile because it removes range penalties and would thus let me stay up to 120 feet away from enemies while I shoot. I haven't gotten a chance to test run anything yet, so I don't know if it is better to have more attacks and kill things fast or better to be good at keeping my distance.

Well, both are good, honestly. The PI would probably, in real life, rather have the distance than a second gun.

[hecetv]

Why survival, isn't that for living in the woods? Instead give him something like religion or arcana for dealing with cults and demons, since I imagine that will come up for a dnd private investigator. Or give him a skill or proficiency he can patch himself up with (pour alcohol on bullet... I mean arrow... Wound, take a huge swig, bandage wound, take a few more swigs and then ruminate over clues in his dingy office).

Or perhaps give him proficiency with persuasion for getting out of trouble.

[Steel Mirror]

His Expertise is in Perception and Investigation and his Human Variant feat is Observant, giving him passive Perception and Investigation of 22 at level 1, and reaching Passive 30 at level 17.That might indeed be excessive, but it's also pretty cool for the character. Depending on the game, I think that sounds pretty cool. If a high level of combat optimization is expected in your game, though, I suppose I'd have to advise against it.


1) Given that hand crossbows have only 30 foot range until you get sharpshooter, is my Con of 8 going to get me killed because I am too close to my opponents?Risk makes life spicier! Seriously though, if you have a good fighting type to attract attention to himself, this will be a challenge but not an insurmountable one. Plus it gives you plenty of chances to complain in character about being too old for this, and smoking being the death of you...right before you light up another one.


2) The following feats seem useful for my build, can I get opinions on them for this build: Alert, Dungeon Delver, Skulker.I love Alert, especially for the nosy gumshoe type. It's one of the number one tricks of enemy thugs to catch you by surprise when you are walking down a dimly lit alley while expositing with a gritty monologue voice-over, and Alert gives you a one-up on the situation. Then again if you go with Observant your passive scores will be godly, so perhaps it's not quite as noticeable an improvement for you.

Dungeon Delver is highly situational. It excels in big dungeon-diving games, but if that is your game then your pulpy private eye is probably going to be feeling a bit out of place. :smallwink: I generally am not a huge fan of it outside of seriously dungeon-crawling games.

Skulker is also one of those feats that is quite situational. Overall, I'm not the biggest fan. Most of the time the first benefit is something that DMs will gloss over, the second benefit is nice but players have fewer chances to take advantage of it than enemies, and the third benefit is nice but darkvision works better, anyway. As you are playing a human that last one could conceivably be useful, but if you are willing to spend a feat to be able to see in the dark, it seems like it might be simpler to play a nonhuman and forgoe the feat for automatic darkvision.


3) Which Rogue sub-class should I aim for? I am currently leaning against Arcane Trickster because I want to dual-wield crossbows eventually, but strong spell suggestions would change my mind. And I am completely split between thief and assassin right now.Assassin's are pretty much my favorite, but if your PI has a bit of a burgling bent then I could see Thief being a decent choice. Assassin really is quite good, though.


4) Considering the archery boost at 1st level, action surge at 2nd level, and improved Crit at 3rd level (and sneak attack doubles on crits, I'm told), would it be a good idea to take a few levels of Fighter? And if so, what amount would be Optimal?If crit-fishing is a priority, level 3 sounds pretty good. I would personally just take it to level 2 for the action surge, but I could also see a case being made to take it to 4 for the feat/ability boost. But I'm supposed to actually give a piece of advice, so I'll vote for the 2 level dip.

[TomPliss]

Assassin's are pretty much my favorite, but if your PI has a bit of a burgling bent then I could see Thief being a decent choice. Assassin really is quite good, though.
Assassin is really Cha/bluff oriented, with the forgery and Deception things, while thief is more about using your hands rather than your face.

[Strill]

The biggest advantage of Thief is the ability to toss out all manner of crazy gadgets with your bonus action. Caltrops, ball bearings, medical kits, potions, magic wands, and eventually magic scrolls. If you can convince the DM to let you come up with a handful of new doodads to use, you'll excel. If you're not much interested in gadgets, then Thief probably isn't the class for you.

As for Crossbow Mastery, I wonder if it's needed for you. It's not a bad feat, but it's not the best for a rogue. True you get two shots, so you can try again if your first misses, but you can already use your bonus action to hide and get advantage on your next attack. It's not quite as good, but it's pretty close, ensures you're eligible for sneak attack damage, and it doesn't require a feat.

[rollingForInit]

If you go for an excessively high passive Investigation and Perception, make sure that your DM will use it to go you all the kind of information you'd get out of a nearly superhuman perception. Obscure details of a room, specific things you notice about people, overhearing conversations everywhere, the opportunity to read lips, etc. Most of which won't be relevant, but it'll make for a fun character. If your DM will only use the passive for traps and hidden objects, taking Observant probably won't give you anything you couldn't get elsewhere.

[Argo]

For a 40s/50s gumshoe character, I'd think you'd want a much higher Charisma.

90% of investigation in those stories is trying to talk information out of people.

[Grayson01]

I love the concept and the Idea off it all.

Just a small quetsion have you thought about Lore Bard instead of Rouge, maybe even Half-elf with the Urchin Background? I think it might give you everything you want and more.

But if not, I think Theif might net you better results then Assassin. Assassin will tottaly help up your Damage out put, and help with going under cover, but the P.I. concept to me dosen't scream death from the shadows style.

Answer to questions

1) Maybe, depends on the party make up and how you use your actions.
2) Those are all great, Alert is awesoem for an Assassin build, DD is right up your ally, and SKulker to me should be a Rouge Assassin class feature.
3) See above
4) The improved Crit from Fighter (AFB ATM) I am pretty sure don't come along until after 3 levels of fighter, and I am not really sure if it is worth it to me to give up the SA Damage and your going to get at least one Crit a encounter if you take Assassin and Alert. It's also only 19-20 increase for the crit so I wouldn't bother with the fighter levels. I would just stick with full rouge.