D&D 5E Need help optimizing a Rogue-based Nova build idea.

NapBass

First Post
I had an idea for a Nova type build that hopes to abuse assassinate when possible while not being completely useless in combat afterward. I've seen the builds that are Rogue/Paladin/Fighter, but I want to go a different route. My take on it is using the new College of Whispers bard from the UA a little while back along with the bladesinger from SCAG for the blade cantrips. At 3 rogue 3 bard 2 wizard that would potentially give me 4d8 + 8d6 damage on a successful assassinate. The damage breakdown is: 1d8 (+x) rapier, 1d8 booming/green flame blade, 2d6 Venomous Blades, 2d6 sneak attack, which is all doubled from assassinate.

As far as the character goes, I was thinking of a gambler type, maybe criminal or something similar. Most likely half-elf with +1dex/+1int. My group uses stat array so this would give me 8/16/10/14/12/16 for stats. With all the expertise I'd get from bard/rogue MC my skills shouldn't be an issue, perception in particular. Alternatively I could go variant human and take lucky at lv1, which would still give me enough stats to multiclass into everything.

I'm wondering how I should level up (thinking 3 rogue 2 wiz 3 bard) and if anyone has any tips on optimizing the character, including where to go with the later levels. I know I want to pick up lucky as soon as possible to decrease my chances of whiffing when I finally get my moment, but I'm not sure if that's worth getting before dipping into other classes.

Also, would it be better just to run paladin or another class instead of wizard or bard? I'd like to make this combo work but if there's something strictly better then I'm open to switching it out. Obviously I'd want to do enough damage to make this whole thing worthwhile.
 

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First Post
Assassinate really needs action surge to have some value.

You really need a way for the rest of the party to succeed at stealth, because if they have to stay away and be mere bystanders you lose more DPR than you gain.
 

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