I’m really at the beginning stages of this. All that I know for certain is that the character’s main alias will be “Willy Nilly”, that I’ll be using the Fey Heritage Feat tree, and that the character will be leaning into the trickster/chaos agent archetype a bit more than my previous Fey PC.
My first question is what (official) D&D PC races lend themselves to a classic Fey character? The list I’ve made so far:
Human
Elf
Drow
Half-Elf
Gnome
Killoren
Hengeyokai
Shadar-Kai
Tabaxi
Kenku
All ideas & commentary welcome.
This is a huge IMNSHO thing, but...
The entire point of playing something with Fey Heritage is to be unearthly, strange, or weird. Not human, but with enough connection to humanity to be relatable and fun to play. OTOH, playing lots of other fantasy races, like Tabaxi, Drow, Hengoyokai, etc, is to to be unearthly, strange, or weird. Not human, but with enough connection to humanity to be relatable and fun to play.
So what they heck is the point of trying to drop a Fey Heritage on one of these other races? One option is powergaming. Which I totally respect, but won't be going into in this post. Another idea is to get a very, very specific Fey/X cross that you want. Like a Fey/Dwarf to intentionally get into an industrial vs nature story arc, or a Fey/Half-orc to make a non-traditional high-CHA half-orc. But none of those options are really playing into the classic Fey trickster/chaos archetype you talk about. They're all things that are something else first, with Fey just tacked on. At most, your backstory is 50% Fey, which doesn't sound like what you're describing.
So, TL;DR, if you want to do a Fey Heritage build that is about being a Fey Heritage character with classic Fey Heritage archetpyes, start with a human base. Focus on the Fey Herritage, not the other race stuff.
Only if you want to be more extreme, consider the Half Elf or Elf route just to start a litlle closer to Fey. But if you really, really want to maximize your Fey side, you should go full on Pixie or something similar with LA (and Savage Species when needed).