In my case, I don't use training because my skills are too low. In fact, sometimes it feels that my skills level too fast naturally.

I use it because (1) it's a good way to reduce my gold and (2) it kind of fits with the roleplaying concept that if you want to improve, from time to time, you need to pay someone more knowledgeable to teach you things.

I actually modded the game to so that there was no longer a reachable limit to training per level.

I like having merchant characters having a viable way to increase their skills with all their wealth; rather than just letting it be there in the inventory screen.

Well, it gets expensive but yes, I train. I do it mainly because I think the game could do with more moneysinks. After awhile, gold becomes rather meaningless, so I try to find ways to spend whatever I can.

I've also found it considerably slower to naturally train Light Armor than Heavy Armor. If you favor Heavy Armor, chances are you're a warrior type and that usually means frontal attacks and taking a beating (hence improving the skill). My sneaky character doesn't get hit very often, so I use training to get that skill up.

I never went to college either because why pay money when I can just get a job and learn while getting paid. loooool

Hello welcome to McDonalds may I take your order?

Pickpocketing is easy to level up naturally without the need to grind. Play as a thief and go around pickpocketing people and you will max the skill out in very little time, compared to other skills. The same applies to alchemy, even without using alchemy improvement enchants.