Stealing and pickpocketing are basically useless outside of doing the Thieves Guild questline IMO

Tsar_Gekkou

I'm only making around 19K a day selling the greens and blues because good stuff almost never drops, but racking up a big bounty is hard unless you're doing it on purpose. I run a setup to minimize detection radius and i'm literally invisible. If I have a bounty, I can crouch into stealth and not get caught while standing on a guard's toes. I don't need to use food or potions at all either. It just sucks that you're better off farming an easier and quicker vet DLC dungeon like Falkreath hardmode and selling the motifs for cheap than pickpocketing.