To me, pickpocket only seems realistic (roleplaying wise) to do at lower levels.I have this idea of a character who starts out as a pickpocket to make money early on, but then sort of abandons it at later levels when he's more powerful.

But the way it works in game, it seems nearly impossible to do at low levels, unless you use the method where you save before every attempt (LAME).

Thoughts? Should I completely give up on this idea? Is there a ring of the cutpurse or something hidden somewhere that I can find rather easily in the first few levels to give me a decent shot at this?

Save before, if you fail, load the save. If this play style is for Rolepay purposes, then it should be fine, just roleplay that he never got caught, and if you don't like that stash your loot in a barrel or something after each pickpocket attempt.

Steal stuff that you can (Higher chance of stealing) put points into pickpocketing.

If you are high level there is also a chance you can get caught. I get caught all the time. You are just better at it and you are more subtle

Yes, but right now the highest I've seen is about 52%

Well, this is stupid. Just realized how much the very first pickpocket perk helps. Right away many items show up as 70% or more....so I should be able to start doing a lot better. Still quite a bit of risk for very little reward, so I don't think I'm going to go this route.

You sure? I like the idea of a crime lord walking through an alleyway and not a single septim is left in there by the time he leaves

I find the best way to do this without getting caught is to grab this first item and close. then go in for more. The longer you search them the greater the chance of getting caught. Also you can use some pickpocket potions that can help a great deal.

That would actually make sense, but it's news to me. I think the whole pickpocket thing would be cooler if the bounty wasn't automatic. Like, if you got caught, run! If you can hide before a guard gets a clear look at you or catches you, you're home free.

The problem with pickpocketing is that it's pretty easy to get caught, and the consequences if you do are extremely harsh. Now, granted, you shouldn't just be able to walk up and steal a giant sword off a guy with ease either, but then, this is a video game.

Agreed. I think it should be easy to be caught. After all you are digging throuh someones pocket. I learned my trick while doing the thieves guild radiant quests. I kept having trouble getting caught because I wanted to see what else I could take while there. I paid many fines before figured this out.

If I were a thief, I would not be a pickpocket. Too risky. 90% success rate is not good enough for me. So much easier to just steal things when people are away from home. And when they find me when I'm in their homes, they just tell me to leave. Good bye, I was leaving anyway.