My strategy for training lower skills is pay for training in desired skill, pickpocket money back, maybe raise some other skills while waiting to level if you haven't already, and then repeat. Goes much faster this way.
Yes, I agree, that works quite well at lower levels. When over 42, however, like the OP, you're not going to get nearly as much mileage out of buying the lowbie skills- so you'll have a lot of work to do until your next levelup. Although if he hasn't done anything with pickpocket yet, a couple of hours of dinking around in a town or two can get that skill from 20 to 75, in a hurry. But that's one of the few quick 'n cheesy skills to level up easily. And quite profitable, too!