I seem to get caught all the [censored] time -.-

Even placing a gold coin on someone while they are sleeping seems to be a challenge. THis annoys the hell out of me because I need 50 pickpocketing for the +100 carry weight perk.

Any advice on a supereasy and fast way to level up pickpocketing?

Keep trying and reloading, or find a trainer. I train a lot of my skills that I don't use regularly.

On Oblivion it often worked if when you were stealing something, you put something of equal weight back on them so they didn't notice, E.G. stealing keys, and putting another key in their pocket.

When you pickpocket you see a percentage for being succesful for every item in the inventory. At low levels you just have to try to steal worthless stuff like food. Later on you can steal the good stuff

yeah go for the high% stuff and do not try to steal from guards or quest npc's. they will most likely catch you but just save right before you do it and try it over and over.

I don't know of any great way to level up pickpocketing other than just start off small and work your way up, or having the money training it with a skill. I recommend starting with the inns and finding sleeping NPC's there, they are usually easy to pickpocket.

Pickpocket the junk items first as this gives you your highest % chance rating. Since your going for Extra Pockets you should get Light Fingers 1 +20% chance and Night Thief +25% chance from sleeping NPCs ASAP (you need them for the +100 carry away).

I've begun training Pickpocket on my level 30+ directly, and I feel silly for training up some skills (Like One Handed or Light Armor) that were going to level up naturally anyway.

Pickpocket is one of the more annoying ones, and leveling it "naturally" just isn't reliable.

Find a trainer, pay for one skill up, pick poket the trainer to get your money back, and then pay for the newt skill up and so on, untill it getts so expensiv to skill up that it gets imposeble to pick poket your money back, this got me to around 30 in pick poket and after that it was easy to just pickopket everyone i saw in the world.