utumno
pickpocket well. look at what is available at a merchant BEFORE ripping them off.
that way you know exactly what that unidentified ring (belt, sword) is.
also, the merchant inventory can become quite jammed up (on the pickpocket screen) so it really helps to know the item(s) you're after.
my suggestion is to always go for the highest value arrows you can find. arrows are split-able.
if you were to pickpocket a gold charm (for instance), that's great - but at lower level just try to find a merchant that has 50,000 gold sitting around to buy it back! no, grab some expensive arrows and slowly sell them off (or trade). this works extremely well.
also please recognize that gold itself is seldom the best option to rip off. <img src="/ubbthreads/images/graemlins/smile.gif" alt="" />