I knowingly fall into the first category - can't tell you on the second. So far I've experimented a great deal, but rejected everything that cost any significant amount of money that didn't make a fairly large quality improvement. Since I've bought a lot of the equipment used, I just sell what didn't make a big enough difference to justify the cost and don't think twice about it.
Interesting question, though. I think your wine analogy shows that there are many areas where this question fits. I bought a floor-model Proton television set one time at a deep discount compared to it's list price, but not compared to a nice Toshiba or something. The picture struck me as great at the shop. Over the first month, I realized the picture was pretty horrible most of the time, but I had spent money impulsively and could have spent less and gotten more. It took me quite a while to admit to myself that it was a waste, get rid of it and get something decent. Such is life. -Kirk