If I am fishing and take multiple items does the chance decrease every catch if the targeted item is at a constant 90%?

If you're asking what I think this is what I've noticed: if you're trying to take multiple items there's a greater chance you'll get caught regardless of what the %-age reported is. Also, higher weight and value decreases your chances.

I only pickpocketed in the Fishing jobs and only did enough to get my Pickpocket to 100, but it seemed to me that I got caught more often when I tried to take multiple items for the hell of it. FWIW: I don't have any perks in the Pickpocket constellation.

I thought it did, but it honestly seems to be random. I can take three pieces of jewelry off someone that have less than a 90% success chance, go out and adventure, come back, pickpocket a different person for some lockpicks and ale and I get caught. I've Pickpocket at 100 and all perks in that tree, so that does factor in, but the rest is still random. I'm able to take everything off a person if they're sleeping and I'm crouching, but that's about it.

My question is: how long does it take for picked pockets to get new stock? I remember they restocked eventually in previous patches but lately no one wants to put more valuables for me to... how to put this? "Admire and acquire"? Yeah, that's a good one.

I wanna bump this because I was wondering the same thing. I recently went on a serious pickpocketing spree to get it to 100 and took most of the perks (except the last two). But now it seems like I've pickedpocketed the inhabitants of Skyrim dry. One second I'm thinking I should be able to get at least an amethyst off this guy in fancy clothes but the next second I find out that all he has is a piece of fish, a lockpick, and maybe a few gold.