For the former, speech, it seems like the only way to really level it up, bar exploiting, is to pay a trainer. There are two primary benefits of leveling it up...One is that you make more money selling loot and spend less buying stuff, which would offset the training costs. The other isn't actually a real benefit aside from convenient - perks that basically let you spend less time running between merchants. The merchant perk is probably the most obvious (HELLO THERE MR. ALCHEMIST, I HAVE THIS WONDERFUL SUIT OF PLATE MAIL YOU MIGHT BE INTERESTED IN...) The question is, is any of this worth it? The primary benefit is that you get more money faster, but I seem to be running around with a lot of money as it is. I mean, I guess I could buy all the houses I know of and pay for training at every level (come to think of it, I should probably have done that before...) but it seems like money is easy to come by.
Pickpocketing doesn't need training to level up but, again, it seems to have questionable usefulness other than giving you more money.
Am I missing something obvious here? It seems like accumulation of money doesn't really help much, and that's what those two skills are for.