I've never actually seen anybody Pickpocket in a legit way, and by that, I mean without saving beforehand. In real life, you try to pickpocket someone and fail, you have to deal with the consequences. And I had wondered if anybody has ever played a "Legit Pickpocket?"

I try to but then when I miss I always think 'No I can't get bounty yet I just want this one thing...' and it sort of indefinitly goes on. Probably the only RP-breaking bad habit I have right now, but it's so hard to not give in and press F9. :c

I haven't tried to "legitimately" level pickpocket, but making the target vulnerable by paralyzing it first and then pickpocketing what you like sounds like a massive time-saver.

Pickpocket is probably #1 on my list of "Skills that take too long to level yourself so you should just use trainers so you won't pull your hair out trying to level it yourself."

I'll try and come up with a more succinct title later.

I have a character that would only reverse-pickpocket items to people she liked (gold ring) and people she didn't like (dead fish) so I really didn't want to incur a bounty when I wasn't taking anything...yes, I'd save before the pickpocket attempt.

I have tried this a few times but the pickpocket % is jacked in this game sometimes. I failed 4 times in a row once with 90% chance of success tyring to pickpocket a small amount of gold. WTF

Yes, I have played this way. The bounty is not that high and gold is a plenty, so it is not that big of a deal. I usually turn off the HUD before I go pickpocketing or breaking into people's houses for a bit of burglery. It is much more immersive that way because you have to look around at NPC reactions and see if anyone is looking at you to know if you are hidden or not. The sneak crosshair is a cheat in my book and makes the game less fun.

The only way I play. What fun is the reward if you remove the risk?

No offence, but probably you don't understand probabilities very well. The chance to fail with a 90% skill is 10% (or 1 in 10) and the chance to fail 4 times in a row is 1 in 10^4=10000, which is non-zero and could happen. For example, the chance to get struck by lightning is about 1 in 300000=3*10^5 (just google it) , which is much smaller but has been known to happen.

The only time I save first is if I am just looking at what is in the NPCs inventory. I think it is OK just to look in this game, but it is an old habit.

However, if I am going to pickpocket someone I don't save first. In fact, even though I post many threads about how to properly manual save, I rarely save the game while I am playing it. Only when traveling to a new area or going into a new dungeon.

Then again, most NPCs don't have something worth taking, so I rarely pick a pocket.