Waiting for price drops and used copies of new games?

Does anyone here have experience with holding out on new games until there are significant price drops or a plethora of cheap used copies on the market?

I opted out of spending the $65 for GTA V at launch, as priorities and budgets have shifted since leaving college. My thought was to wait and get a cheap used copy around Christmas, as I am already seeing used copies go for $44 on Amazon.

My expectation is that GTA V will have a huge used copy market in several months, as many teenagers become bored with the game. Does the game experience take a hit, especially online, for games that are picked up later in their life cycle?

I am accustomed to rushing out and getting the new games and playing them to death, but I can't drop that kind of money on games anymore. Does anyone else do this?