I feel as you do. I'm moderately well-off, not because I'm highly paid but because I know how to be efficient with money. Paying close to 400 bucks to play one expansion is nothing of the sort.
I will upgrade when one of three things happens:
1. My PS3 breaks or is stolen, or otherwise becomes unavailable/unplayable.
2. A super-awesome game comes out for current-gen, one I just can't do without. Like Fallout 3 was for PS3.
3. I find a PS4 or Xbox 1 under my Christmas tree or some such thing. Unlikely since I'm the only gamer in my family.
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I'm the same way. I'm considering trading my 360 and all the games in to see what I get for it though.