98% of the time, I'll play a game "vanilla" first before modding it for the next go-round.
There are minor exceptions - like, I played Oblivion awhile after it came out, and just after playing a modded run of Morrowind. There were more than enough "OMG! Oblivion level scaling BLOWS!" comments, that I did my first play with a scaling mod. Or Fallout:New Vegas - as soon as one was converted over from Fallout 3, I installed a body mod.... which was purely cosmetic and modified nothing that I didn't already know all about (since the bodies in FO:NV were the same as in FO3)
Since nearly every single RPG released in the past 10 years has had the same problem of being way too easy to get rich, I would be extremely shocked if a mod to increase merchant prices is not required for Skyrim.
Hmm, odd. I've never noticed being "too rich" in games. Probably because it doesn't bother me if I have lots of unused cash lying around - not having anything to spend it on isn't really an issue. Probably because the games where you have "lots" of money? There isn't anything you need to buy anyway (after the first few levels) - you get everything useful from looting. Money's just a "score" you can use to trade brags with people. :shrug: