Torn on rogue subclass, optimization help

[Taebyn]

I am looking at maximizing my sneak attack opportunities for my rogue. There are many ways to do this. The subclass and weapon choice really seem to divide the concepts I was working on. So I was looking for some input as I like both builds.

Disclaimer: The campaign I’m in runs home brew exhaustion rules. The first level isn’t debilitating and can be cured with a long rest. There is a lot to this but I don’t want to divulge a lot of the work our DM has done. We are also on gestalt level 2 characters. With that in mind we are running a lot of deadly encounters, hence this back up character I’m making. So when I reference a multiclass imagine two free levels before the dip counts against normal level progression. I don’t want to go to multiclass 5 for extra attack as it delays my multi sneak attack opportunities until 16+ barring relying on others or reaction. So I need to get extra attack from my bonus action via crossbow expert or dual wielding.

Thanks for getting through all that. Here are my current prospects

Arcane trickster
(I wouldn’t take find familiar as we have a pact of the chain lock and help every turn is kind of cheese)
The goal would be to selfbuff with haste. Normally I hate this spell but god does it shine for rogues. The ability to sneak attack with the extra attack is insane. Then holding your normal action to sneak attack on someone else’s turn is just filthy. This comes online around level 14 depending on multiclass. I’m leaning toward battle master multiclass for precise strike, riposte, trip attack. With two gestalt levels in fighter the build would be fully online at 15, we are at 10 now. My weapons on this build would be shortsword and whip. I’m just not a fan of rapiers. So dual wielding to get another attack if I miss. Im not sure if I should just be using booming blade and and accepting misses or not ever using booming blade to have the option of a bonus attack.The whip with sentinel is pretty enticing.

Pros: sentinel/whip/riposte/trip attack synergize really well before haste comes online. Shadowblade and booming blade seem pretty thematic and super effective. Okay, spells in general.

Cons: mellee, whips are loud you dumb rogue, maximum operating tempo gives exhaustion, booming blade is loud you dumb rogue

Scout
Gets to sneak twice a turn at 17. Comes online pretty late but doesn’t require expensive buffs. This build would also be a battle master multiclass. The focus would be hand crossbow with crossbow mastery. Just as before, a bonus action attack when needed.

Pros: very mobile for kiting, archery fighting style consistency, Sharpshooter nets a lot of dpr for you (sans consistency comment) just a very efficient clean feel to the build.

Cons: a bit bland (personal bias?) loses a lot of reaction opportunities to being ranged. There may be some weapon drop shenanigans to hold a mellee weapon to threaten people, but that’s not really my style. Comes on really late and doesn’t have much in the arsenal for variety until then. Could go magic initiate/booming blade/warcaster/ whip dual wield but why scout that point?


Hexblade
Jk

Conclusion: I have tried mixing up the weapons and fighting styles between the two subclasses and I feel that crossbow mastery doesn’t offer as much as dual wielding with a whip and sentinel. The scout could be ran as mellee and move away after making an enemies movement 0, but I’m looking for some different viewpoints.

[CTurbo]

Swashbuckler with 2 free levels of Draconic Sorcerer.

Swashbuckler means you get sneak damage pretty much every turn. Draconic sorcerer gets you 13+dex AC, Booming Blade, and some other fun spells.

You wouldn't have to multiclass out of Rogue but 5 levels of fighter is always great, and Swords/Valor Bard would fit too

[CTurbo]

Gloom Stalker 3 or 5 and Assassin 15 or 17 with 2 free levels of Fighter

Take Archery and TWF so you'd be great at both melee and ranger. Have super stupendous first turns. If you went Ranger 5, you could have 7 attacks on your first turn with an Action Surge all with advantage and all auto crits if the target is surprised.

Sentinel is a must since you can get another sneak attack with your reaction.

Booming Blade with a whip is awesome. You just need Warcaster and Spell Sniper to pull it off.

[JellyPooga]

Have you considered Barbarian for your Gestalt? The extra HP over Fighter are relatively insignificant, but the Advantage on Athletics checks and Reckless Attack means that whether you're grappling or attacking, you always have a decent chance of connecting. The additional damage and resistance to B/P/S Rage offers is very tasty if you're thinking of sitting on the front-line much.

Have you also considered Thief Archetype for your Rogue levels? Fast-Hands is a resource-free battlefield control ability so long as there's any kind of terrain available. Break branches off trees, topple bookcases and turn chairs to create difficult terrain, throw water on fires to extinguish lights or create clouds of steam (obscurement), not to mention being able to use equipment, all as a bonus action. Thief also offers two turns for the price of one at the tippy top of the tier-tree; if the campaign is going that high, that's an ability holding out for just as much as the Barbarians capstone or 9th level spells. Supreme Sneak and UMD aren't an awful lot to shout about, but the latter, at least, can be very useful in the right game/with the right magic gear.

[Orc_Lord]

Barbarian 3 / Rogue can be pretty sweet. Reckless attack gives you advantage ,so you can always sneak attack.

Bear totem gives you super survivability as well. Just realize that some abilities only work with Strength.

[Corran]

There is no synergy between whip and sentinel. That's because sentinel grants the reactionary attacks only against enemies within 5' of you. So you need to be adjacent to an enemy, thus the reach of a whip does not offer anything.

That said, if you want to proc sneak attack with reactions, there are basically two ways I can think of (both of which you mentioned), assuming you don't want to rely on allies (such as a battlemaster with the commander's strike aneuvre). One is to go melee with sentinel, but that doesn't work well IMO if you don't invest 5-6 levels in fighter and if you don't go S&B. The other way is through hasting yourself, but that works much better in range (easier to set up and direct a ready action, and less risk to losing concentration which hurts a lot).

ps: Trip is of little value to a rogue, better go with the feinting maneuver which will be useful when you need to cancel disadvantage, or with something else.

[CTurbo]

Battle Master with Riposte is a reliable way to pull it off too.

A Swashbuckler/Battle Master with Sentinel should be able to get off two Sneak Attacks almost every round. Just go stand by your buddy. You attack with your reaction whether the enemy attacks you or your buddy.... well if he misses you anyway lol

[solidork]

I would 100% do a Arcane Trickster/Bladesinger multiclass in this situation. Haste comes online much sooner, you get way more slots and versatility plus all the benefits of Bladesinging. Be sure to pickup the free proficiency in Scimitars and then try to get a Scimitar of Speed for double sneak attack all day every day, no haste required.

[JellyPooga]

There is no synergy between whip and sentinel.

I disagree. While true that Sentinel only triggers at 5ft, that doesn't make the additional control that whip offers with reach obsolete. Rogues really like OA's and Sentinel offers them more, as does the Whip. A Rogue with a Whip and Sentinel is an OA machine.

[CTurbo]

I would 100% do a Arcane Trickster/Bladesinger multiclass in this situation. Haste comes online much sooner, you get way more slots and versatility plus all the benefits of Bladesinging. Be sure to pickup the free proficiency in Scimitars and then try to get a Scimitar of Speed for double sneak attack all day every day, no haste required.


How does a Scimitar of Speed offer double Sneak Attack?

[Taebyn]

Thanks for all the replies. I am pretty set on battle master mc and either AT/scout. I was mainly looking for suggestions on weapon choice and subclass. I’m open to all of it though. Thanks


There is no synergy between whip and sentinel. That's because sentinel grants the reactionary attacks only against enemies within 5' of you. So you need to be adjacent to an enemy, thus the reach of a whip does not offer anything...

Creatures provoke opportunity attacks from you even if they take the Disengage action before leaving your reach.
So I would be taking sentinel anyway when dual wielding to capitalize on opportunity attacks on my adjacent party members. Since I’m dual wielding a whip if an enemy leavesmy whip range, wouldn’t they invoke attack of opportunity?
As far as trip attack goes, I was torn between it and maneuvering strike. I was hoping to create some advantage for the other melee party members.

[Corran]

Since I’m dual wielding a whip if an enemy leavesmy whip range, wouldn’t they invoke attack of opportunity?
They would, but remember that you have only one reaction per round. And you want to use your OA against a fleeing enemy that has an ally of yours adjacent to them, so that you can use sneak attack dice with your OA. IME this is far more likely to happen against enemies within 5' of you, than against enemies at 10' from you.


About using sentinel on a rogue, have a look at this (http://www.giantitp.com/forums/showthread.php?496792-Theorycrafting-sentinel-rogue) if you are interested (there is a lot of value in the comments).
The thread is old, and if I were to build sth like this today I would definitely go for more battlemaster levels (probably 6) than what I mentioned in the op.

[Taebyn]

They would, but remember that you have only one reaction per round. And you want to use your OA against a fleeing enemy that has an ally of yours adjacent to them, so that you can use sneak attack dice with your OA. IME this is far more likely to happen against enemies within 5' of you, than against enemies at 10'

I am aware. I still disagree about there being no synergy. While you want to use your reaction that way, it’s not always the case. I think the whip adds to possible action economy and thematic elements imo. What’s kind of discouraging is hearing that trip attack wasn’t very effective for you. I’m guessing mileage may vary but thanks for the link.