So the original post on reddit had title “Just because I’m an overgrown puppet cowboy seeking “his favorite deputy” doesn’t mean I’m unable to do 4d10+12d6+30 damage in first turn of combat” but I fucked up the math. So I’m finishing it. Assuming Woody is Gloomstalker Ranger 5/Assassin Rogue 5, Custom Lineage with Pierce, Sharpshooter and maxed DEX, using a revolver, he could do 16d8+12d6+45 damage. Effectively shooting BBEG a new asshole next to the old one. If he also had two levels of Fighter, he could do twice as much.
I’m usually not on board the “play an existing character” train but I’ll be damned if this doesn’t sound fun as hell.