Tiefling Provocateur

[ZenBear]

I'm trying to construct a moderately optimized build that focuses on fitting a particular character; that of Deimos the Tiefling Guild Merchant, specifically an arms dealer. He is a Charismatic man that likes to play into his fiendish appearance and be a lightning rod of controversy, but with a fervor and charm that gathers followers to his point of view. I would prefer him to be Dexterous, either wielding a crossbow or a finesse weapon (perhaps finesse longsword?), but he will also have Vicious Mockery, Charm Person and Enthrall from the Devil's Tongue racial trait.

A few classes I'm considering:

Bladelock. Perhaps he owns an ancestral blade linked to his Patron. I would like the longsword here because I don't really see a rapier as a good fit and I don't know how well Dual Wielding works with a single Pact Weapon. Armor of Agathys with the Fiend Pact will keep him alive, but what other spells would fit the theme? No need for Eldritch Blast really but it's better than throwing a dagger or drawing a ranged weapon I suppose.

Purple Dragon Fighter. This could be a Crossbow Master build, start with 14 DEX and 16 CHA, rely on Archery Style to cover the difference on to hit rolls, pump DEX at 6, Inspiring Leader at 8.

Vengeance Paladin. I'm considering this one alongside a Cleric of Selune, so perhaps being blessed by, but not beholden to, Shar to seek revenge against the monsters that destroyed his home and livelihood will make for some interesting tension.

Swashbuckler Rogue. Dual wield short swords/daggers/scimitars, use Devil's Tongue and Panache to lean into the provocateur role. Pump DEX at 4, Inspiring Leader at 8, Mage Slayer at 10. So far my favorite, but I might be convinced.

Bard. Lore if I want Cutting Words, Valor if I want him to be more warrior. Some redundency with Devil's Tongue, maybe trade back for Infernal Legacy. I don't like the singer fluff, but it can be ignored in favor of rhetoric.

Thoughts and opinions?

[Specter]

I'm currently playing a Lore Bard 5/Rogue 1 Tiefling. My favorite character ever. Devil's Tongue is not redundant, because it opens up a cantrip and two spells of your choice, which a Bard really needs. Most of the time, I'm spamming Hyp. Pattern or Suggestion, and sneaking in when spells run out. Pretty neat.

As for roleplaying, it can go many ways, but on the social side Expertise goes a long way. That's why I added the rogue level.

[EvilAnagram]

I think the Warlock will serve you best. I would stick with Dex weapons since it's less MAD. If you're not fond of a rapier, go with a scimitar (only 1 less point of damage on average) or see if your DM will let you have a weapon that is identical to a rapier mechanically but is a slashing weapon like a sabre.

The Invocations are extremely useful and would do a good job tying your character's concept to specific mechanical tools.

Have fun!