D&D 5E Two Builds - Barbarian/Rogue & Rogue (trickster)/Wizard (Illusionist)

Greetings! I have a couple ideas bouncing around that I wanted to throw out there and get some feedback on. The game will have a 33 point buy system, in lieu of the usual 27 so that opens up some more MAD builds. If it would be better to have two separate posts, let me know and I will split it up.

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1. Barbarian 12 / Rogue 8 (Barb 8 / Rogue 8 / Fighter 4), Human

What are we losing out by multi-classing with Rogue instead of going straight Barbarian?
1. +1 Rage Damage
2. Persistent Rage
3. Idomitable Might
4. Primal Champion
5. Level 14 path feature
6. Loss of 16 hp (average)

What are we gaining from multi-classing to Rogue?
1. Expertise
2. Sneak Attack (build dependent)
3. Cunning Action
4. Uncanny Dodge!
5. Evasion (you already have advantage on dex saves, this just makes you that much more un-killable)
6. Assassinate (this does not just apply to finesse weapons! Autocrit + Brutal Critical = )

What about sneak attack? That doesn't work with a Greataxe! BUT it does work with your hand axes! I think going 12 into Barbarian, might be a bit too far actually. I might go only 8 (extra attack, feral instinct, ASI), and take the remaining four levels in Fighter. Ideal set up? Javelins or Handaxes for Sneak Attack, Glaive (or other polearm), take PAM feat at level 4, Sentinel at 8, +2 dex, +2 con, +2 dex. I am on the fence with taking Sentinel. You would have to use a finesse weapon to get the most out of it.

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2. Rogue (Trickster) / Wizard (Illusionist)


This build I am not as sure about. He is an infiltration expert (with the Charlatan background) specializing in high profile assassinations. In public, he acts as an private investigator / bounty hunter. He also has a strong connection with the Zhentarim.

How many levels should I take in each class? Is there another class I should be thinking of taking? What else can make this character excel?

With regards to the first build, brutal critical and assassinate don't really synergize that nicely. I mean, if you want to sneak attack, you're using nothing bigger than a rapier, so you get a bonus 1d8 per attack, but for every two levels of rogue, you get another 1d6 on your sneak attack every turn plus 1d6 more on the critical.

For example, let's say you're 8 barbarian/8 rogue. Take one more level of barbarian and you get Brutal Crits and two levels of fighter for action surge. That lets you make at most five attacks on your surprise round and get 5d8 more from those crits. Or spend those three levels on rogue and your better sneak attack will do 4d6 on the surprise round, plus 2d6 more on every other turn.

There's a particular build involving half-orc, only 3 levels of rogue, probably 3 levels of fighter, and a great axe for ridiculous criticals, but I feel like you're better off with reliable sneak attack dice than big crit dice if you're going deep into rogue.

Similarly, does a barbarian with a huge health pool that takes half damage from physical, already has strong dex saves, and maybe even takes half damage from elemental damage really need Evasion and Uncanny Dodge?

IMO, either go three levels in rogue and deep in barbarian to make a critmonster and leave finesse fighting behind, or ease up on barbarian after you get extra attack and be a feral ninja. Either one benefits from a few levels of fighter.

As for your second build, how deep you go depends on how you want it to play. Obviously you need to go deep rogue if you want martial effectiveness, but if you want to beguile and mislead with magic, cool spy spells like Modify Memory need 9 levels of wizard. Illusory Reality has great possibilities, but it's 14 levels in.

For the ultimate sneakmage, try pairing arcane trickster with sorcerer. One reason: Subtle Spell. Well, Heighten Spell is pretty good if you're trying to force, say, a Suggestion spell down somebody's throat, but Subtle Spell will let you cast spells from the shadows without revealing your location, or enchant people to their face without revealing you're casting a spell. It's a little MAD, so I suggest either dumping INT if you're going deep spellcaster, or keep CHA low and only grab enough sorcerer for the metamagic.