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.