An easy way to get free training is to simply buy the lessons, then pickpocket the money back. This worked wonders for my thief, who could hardly ever find the time or situations to level smithing, one handed, and light armor.
However, once you get to level 51 in any skill, the price for training TRIPLES! At level 50 it's 500 something, then once you go to 51, it goes up to almost 1600 gosh darn Septims!
Now I understand this isn't really an issue for those of you who loot anything and everything, do tons of dungeon raids, are a high level, and have enough Septims to crap on. But due to RP constraints, my character is always very low on money, not usually carrying more than two or three thousand gold at a time. Plus, with the price inflation, pickpocketing the money back is buttloads harder. Even now with my pickpocket skill finally at 100, I only get about a 20% likelihood of "getting my money back."
Anyone else have a problem with that sudden squeeze out of their coin purse?