What is the best way to increase pickpocket skills without getting a bounty? I'd pickpocket bandits but I'm usually too busy not getting killed by them.

Follow your target, take nothing under 80% til you raise your pickpocket .. take a nice trip to Windhelm and use the trainer their... take some money or chop wood. While I raise my pickpocket with charm's and such.. I don't use them while I am trying to raise it.. only for the stuff that the character is likely to get caught taking.

Pretty sure the chopping wood is for money which then can be used to buy training in Sneak.

err no

yes... Sorry I am often short.. on words...lol

If you stick with somewhat low cost items you can generally get people to accept your surrender and the bounty will be there but not actively pursued.

What others have said, pickpocket guards of their arrows and whatever else has a 90% chance. When you get to a high enough pickpocket skill (I'd say 50+) start pickpocketing Redoran Guard soldiers in Raven Rock, you'll get more xp for their elven arrows. Past pickpocketing 70 (where you can nick weapons) take their elven swords and basically any weapons people in Raven Rock are carrying (which tend to be better than in Skyrim). If for any reason you don't get more xp for higher-level steals, you'll at least make some more money

EDIT: also steal from the Skaal, a few of them tend to have Nordic or even Stalhrim gear to take.

It also helps if your target is sleeping. I never had good luck with the arrows off guards but sleeping targets generally pay off. I found at least one place where there were many, many people sleeping and made really good progress.

Pickpocket everybody, just make sure you have enough gold to pay off your fines when you get caught or don't mind jail time... because no matter how high your level you will get caught there is no such thing as 100% chance of success.

And when your level is high enough you'll usually be able to steal it right back from them. 500 septims, ta!

You can kinda cheat it up when you have a bit of Pickpocket levels........oh, and a bit of gold(1k or so on hand).

Do you get credit for giving items as well as taking? I could always find a sleeping person and give an arrow then take it back.

I don't believe you get credit for giving stuff back.

As an aside, the perk for placing poison limits you to just one dose per pickpocketing attempt. I played an assassin once and though she could place several potions at once and kill the target, but no go. It makes sense (I guess) but it was very disappointing.

It helps to cast a calm-spell of them first.

Of course, on higher levels, you have to put perks in illusion to make the spell still work on the bandits and foresworns. And then, your character is more of a nightblade than a pure thief.

As far as I remember my own attempt:

If you put two bottles of Frostbite-Venom in someones pocket, only the first make damage, the other stays in his inventory.

BUT if you put one Frostbite and one other poison, he suffers both!

OH! I never though to try different poisons instead of multiple doses of the same poison. Darn! My assassin always had a bunch of different poisons, too. Thanks for the clarification, I'll try to remember for a future build.

I'm not sure the best way to pickpocket without getting bounty, but fastest way is definitely to use a trainer to train up one skill point, then pickpocket the training money back, train up another skill point, pickpocket the money back, etc. Some fortify pickpocketing enchantments will help with the success of that early on. Such as Thieves Guild armour