Multiclass Rogue Needs Some Help

[Magister]

Been going back and forth on my build for about a week and need some advice. I am currently a level 3 arcane trickster and I want to dip into either sorcerer and warlock or warlock and wizard. This all started with my halfling arcane trickster taking a beating(got trapped in a sewer while blind after shawshanking my way to freedom and had only 2 hp left at level 2) and being saved by a lucky roll... I decided to really lean into that concept of luck as both to rp and use with my skill sets. Searched through some classes(was tempted by divination wizard) and found that the sorcerer’s divine soul feature to have guidance, bless and the 2d4 to my save/attack rolls followed by a lucky feat seemed perfect for the concept. I then started feeling like my arcane trickster could use more protection and read about how the shadow blade was so fantastic for my rogue but it would take me until level 7 to get it and the limited spell slots for it with AT was just a bit frustrating so I looked into the warlock stuff and fell in love with those invocations and it felt right with the illusion/tricks/devil sight/darkness for my arcane trickster. Going rogue warlock sounds great but so does rogue sorcerer and rogue wizard... I can’t figure out whether to double class or triple class to bring the concept and character to life without shooting him in the foot. I know the campaign probably won’t reach 20 so I would like to figure out some really fun/crazy multiclass combos to benefit my rogue without crippling him too much. I am a new player and just seeing all the combos is inspiring. I’d really like to know but how best to optimize what I know isn’t an ideal build. How do I best make the character I want within the rules of this game level by level? I want the character concept to shine with being blessed with luck, have that variety without being left behind and cover his weaknesses. He is squishy and has nearly died every single session till recently due to me getting used to using my bonus action to dodge/disengage/hide. I have spent hours looking through the internet and looking at the classes and trying to get everything I want seems so hard without multiclassing at least 3 times... My DM says I can reroll my character up until level 5 and I just don’t know which way to go with my halfling. If you guys have any advice or thoughts then I would really appreciate it.

[Reevh]

Your formatting is hard to read, but I can confirm that an Arcane Trickster with a few levels in Hexblade Warlock can be an exceptionally strong build.

I had a level 11 Arcane Trickster with 2 levels in Hexblade. He used Shadow Blade with a shield most of the time, was an elf with elven accuracy, and had mobile (45 ft of movement without dashing). So he'd dash into melee, make a Booming Blade attack that would do 2d8+2d8+5+4+6d6 damage, and had a nearly 30% chance to crit if Hexblade's Curse was up (and almost 15% chance to crit if it wasn't), and an incredibly small chance to miss. Then he could just step back out of melee, and still had a bonus action if he wanted to dash, disengage, hide, whatever. If the enemy moved to try to get to him, they'd take another 3d8 damage.

On top of that, he had a 21 AC (+2 leather armor, +5 Dex, shield), the ability to cast Shield to bump that up to 26, evasion, uncanny dodge, and 2 invocations, and 2 spell slots that refresh on short rest, and a familiar, along with all the skill proficiencies/expertise rogues get, and reliable talent. He also had 3 level 2 spell slots (mostly used for Shadow Blade) and 6 level 1 spell slots (4 from AT, 2 from Hexblade that could refresh on short rest). Mostly spell slots were for Shadowblade or for Shield, but occasionally other uses came in handy, like Phantasmal Force, Blur/Mirror Image, or Silent Image.

He was an absurd character. Unfortunately the campaign fell apart shortly thereafter, so I didn't get to do too much.

(Actually he'd gotten a lucky pull from a Deck of Many Things and had a 22 DEX, so the numbers were better than that, but I wanted to show what they could be with a normal DEX).

Now you're obviously not playing an elf, so you can't get Elven Accuracy, but even without Elven Accuracy, it's a very viable and powerful build.

[The Big Bear]

The only character I have played is my Lightfoot Halfling Arcane Trickster 3/Celestial Warlock 2, which I am really enjoying. I’m going more for jack-of-all-trades toolbox type character.

More info:
- Good for battlefield control. My unrestricted spell for Arcane Trickster is Fog Cloud, which has been used to great effect to turn the tables in our favor in many fights. I can’t stress how useful this spell has been.

- Good for scouting. Paired with the druids pass without trace and various wildshapes, the two of us can recon quite well.

- Good for support. Celestial warlock gives me Healing Light, used to help party members stay alive in a few cases. We have a life cleric and moon druid that can heal as well, but the druid tends to be in bear form and can’t always heal. Having my warlock help the life cleric in healing has been a good aid to the party.

- Good for damage. Can usually pull off my sneak attack with a light crossbow, giving 1d8 + 2d6 damage. Add hex for another d6. Can also make good use of booming blade for 2d8 + 2d6; add hex for more damage and BB gives some enemy movement control or extra damage.

- I have two spell slots that regen on a short rest and two that regen on a long rest. I can cast Cure Wounds before a short rest and get the slot right back.

- My invocations are devils sight and eldritch sight. I can see better in the dark than those with dark vision, which make scouting easier. I can detect magic at will; it hasn’t come up too much yet but having it there is a cool concept for me.

- My patron is the Lady Luck, Tymora. I really play up luck with my character. Remember to ask Tymora when you need good luck and to ask Beshaba when you need to avoid bad luck.

Since multiclassing into warlock I feel less restricted with my spell slots. I can use the short rest warlock slots pretty freely, then have my trickster slots for emergency use. I’m another level I get level 2 slots; I plan to take darkness and either invisibility or shadowblade.

Hope this gives you some inspiration on making a pact!

[Reevh]

Yeah, Devil's Sight is surprisingly useful in a surprising number of situations. Just having 120 ft of full color vision is great, even if there's no magical darkness around.

[Whit]

Knowing your stats would help. Your already pushing Intelligence and dex. And will need charisma 13? Fir multi class warlock or sorcery. So if you have it, it works. Hexblade lvl 1 is all you need without invocations. If you want 2 invocations then dip fir 2nd but I don’t think it’s worth it. If you went sorcerer yuh need to get dragon fir armor. Which gives resist but you also need to dip more to get the 2 meta magic. Personally. I’d go hex fir better melee as stated above. But cone up with a good reason fir warlock dip. It’s boring and optimized to just get it with no story.

Perhaps a voice whispered to you in the sewers that actually helped you. But you thought it was just luck and your own subconscious. But no. It was a shadowy thought belonging to X who saved you after a panicked and hurried deal.
“The rats ! I’m going to die from rats in this stinking ancient sewer. I don’t want to die down here all alone.” You’re thoughts scrambling quickly as you sought a way out. Near death and bleeding profusely.

A shadowy voice echoed in your mind. You can live young one. Do not despair. I shall keep you safe...fir a price. Agree and it shall be so.
“Yes, I agree. I want to live.” You whisper in a soft laugh. Thinking your near death has muddled your thoughts. I’m rambling, talking to myself you think. Of course I’ll make it. I want to live.

[Reevh]

Knowing your stats would help. Your already pushing Intelligence and dex. And will need charisma 13? Fir multi class warlock or sorcery. So if you have it, it works. Hexblade lvl 1 is all you need without invocations. If you want 2 invocations then dip fir 2nd but I don’t think it’s worth it. If you went sorcerer yuh need to get dragon fir armor. Which gives resist but you also need to dip more to get the 2 meta magic. Personally. I’d go hex fir better melee as stated above. But cone up with a good reason fir warlock dip. It’s boring and optimized to just get it with no story.

Perhaps a voice whispered to you in the sewers that actually helped you. But you thought it was just luck and your own subconscious. But no. It was a shadowy thought belonging to X who saved you after a panicked and hurried deal.
“The rats ! I’m going to die from rats in this stinking ancient sewer. I don’t want to die down here all alone.” You’re thoughts scrambling quickly as you sought a way out. Near death and bleeding profusely.

A shadowy voice echoed in your mind. You can live young one. Do not despair. I shall keep you safe...fir a price. Agree and it shall be so.
“Yes, I agree. I want to live.” You whisper in a soft laugh. Thinking your near death has muddled your thoughts. I’m rambling, talking to myself you think. Of course I’ll make it. I want to live.

My dip was unplanned. Happened because my character died in a fight (the first death in the campaign) and when revivified, we got a new level almost immediately, so I figured that the Raven Queen probably helped me come back, and she's associated with Hexblade Warlocks. Had a look and decided it looked fun, so I did it. Didn't realize at the time just how absurd it would be.

[Whit]

Nothing absurd about it. A lot of times those are the characters that people remember best. My group still talk about certain player characters from long ago that were amazing. Some are even used as NPC’s.
Have fun with it by just playing. But if you want to make it memorable, work with the dm to make it so.
It doesn’t have to overbear other players either. Once in a while having the dm saying a voice in your head whispers X. And when that happens you behave certain way. Crazy , scared., mumbling about shadows. Or that ever suits you. It gives a laugh to the group and adds to your characters mystery story etc

[Keravath]

I have an arcane trickster/warlock that I really like playing. He eventually took warlock to 5th level for pact of the blade, thirsting blade and 3rd level spell slots though for role play reasons he is a fey warlock rather than a hexblade (which might be mechanically a bit better). Having the extra attack can really help with landing sneak attack rather than having everything riding on one attack.

In addition, combining the 3rd level spells from warlock with the level 9 ability to hide and force disadvantage on saves works exceptionally well with things like hypnotic pattern. Even magic resistant creatures have to make a straight save though my DC isn't that great.

The warlock levels also allowed me to take devils sight since this avoids disadvantage on perception checks in total darkness since you can see perfectly unlike a character with just darkvision. It is convenient to be able operate efficiently in the dark and still fully see and disarm traps or other obstructions as well as spot secret doors.