There's a pretty big roleplaying aspect but it can have surprising combat applications.
You have a 100% chance of pickpocketing enemies if they are ragdolled or getting up from the ground - even if they are in combat. This means that at any point you are in combat with someone, you can Fus Ro Dah, run up and take everything they have with no chance of failure. Even their equipment, if you have the top two perks. Paralyze also works, although you can't actually pickpocket until it wears off and they try to get up.
Two stipulations: if they've "already caught you," it doesn't work. This can happen if they readied their weapon and went "I'm warning you" as you approached. Not sure why, but them's the breaks. Also, you can't pickpocket equippted items if they "see" you. This doesn't mean you have to be hidden; I just step behind them while they're still down and can take everything.
train a skill, pickpocket the money back, lather rinse repeat. This also can help you to gain levels quickly as each time you pickpocket your gold back, you are practially guaranteed a pickpocket skill up.
PSN: Davelicious GT: DavePeesThePool NEW SETUP: http://i231.photobucket.com/albums/ee174/Davelicious406/DSC02294.jpg
pickpocket plus thieves guild = lots of money. i just started a pickpocket/stealth/archery/no magic or enchanting/ thief RP character and it is alot of fun. stealing gems and jewelry off of npcs nets alot of cash as long as you have a fence to sell to. The fast skill increases do cause you to level fast so watch out for leveled enemy strength when you hit the dungeons if, like me, you hang out in the cities and level up to about 20 with just pickpocketing, speechcraft, a bit of archery, and stealth.
"Censorship is telling a man he cannot eat steak because a baby cannot chew it." Mark Twain gamer tag = Public Dfndr
U can use pickpocket to steal armor/weapons from high level NPCs and make them defenseless, so i would say it's very viable.
Also, speech is completely worthless and waste of perks don't bother with it.
Putting 3 perks into speech to be able to sell any item to any merchant saves you a ridiculous amount of time when you're selling off your loot, especially at higher levels when just a couple items can clear out a merchant's gold.
It levels up very fast so it isn't too much of a hassle. It hasn't really been that useful though, even with all the perks. The only real use I got out of it is getting a second Blade of Woe. NPCs just don't carry anything worthwhile.