It did bother me when I upped my sneak skill using the monks in High Hrothgar. The problem I have is wanting to play a character that is already developed - who has the rich history and experience I imagined - but then needing to spend the early parts of the game developing.
I sometimes may try and incorporate the development into the story (like my assassin is going out into the world to test himself - and therefore will be able to develop as part of the experience). In that case i avoid the glitchy level up for the sake of RPing.
Or I sometimes might decide to start the roleplying after the character has been built up a bit.
I do the same thing as Ben. Although with smithing, enchanting and alchemy sometimes I level those naturally and sometimes I power level them depending on my mood. I don't like playing a character who has to do all 3.
Getting a skill to 100 doesn't bother me as much as feeling a build is spread way to thin. I think a build feels more complete if there are a few skills that are filled out, but that doesn't necessarily mean they have to get to 100.
For example: Taking 3 points Alchemists, 2 in speech, 4 in one handed and 1 in block. Just seems so spread out and worthless. I would rather take 5 in Alchemist non in speech and 5 in one handed.
Depends what skills (I'm never seeing Relfect Blows, ever). Yeah, I know the advantage of focused skill set but I prefer multiple skills that complement each other really well (I don't mean the Alchemy/Enchanting, obviously). But it's just a matter of personal preference.
I agree on most parts with Ben. However, I usually avoid using trainers for certain skills simply because of the characters I plan out.
For example, let's just say you were playing an abandoned youth who had to fend for his/herself out in the woods for years, I might avoid using an archery trainer simply because I've decided he simply learned the way of the bow through his trials. That being said however, if it doesn't conflict with anything when I'm doing a serious RP, then I'm going to train the crap out of a skill whenever I have the spare gold/time.