Here is another boring way:
Find a master trainer, train, pickpocket, train, pickpocket, fail, reload, pickpocket, train etc... AND HERE I AM IN WHITERUN WITH 90 IN PICKPOCKET AND 50 IN ONE HANDED... and still cant fight due to zero armor... unless i hype it too
works even better if it's a companion (not the guild some1 who follows you)
like Aela can teach archery and you can just take the money back by trading with her XD
not sure the pickpocketing would be a bug though (or the trading, though it makes it a bit too easy)
makes sense you can steal back money after giving it