I would hold off on a PS3 for now. I know it's hard. I want one too, but the reality is that right now SONY still has a lot to prove with it, and it's loosing support, which is not a good sign. I would keep enjoying your PS2 if I were you. There are so many great titles for the system that you really can't go wrong, and what's best of all is that right now you can get them all dirt cheap, because retailers are liquidating their PS2 inventory.
If you wanted to sell your system, then I think $100 is a fair price for your hardware bundled together. Maybe, a little more if you still have the original documents, packaging, and everything it came with. As far as the games go, how much you will be able to get for them really depends on what printed edition you have. If you anything that was reprinted in the "Greatest Hits" line, or is a "Greatest Hits" edition, then you won't get squat for it. Maybe $15 tops if it's in excellent condition, unless you have an original printed edition (the one with the black Playstation 2 border on top) in good or better condition, and you're selling to a collector. You will get more for the games selling them individually on either Amazon.com or Ebay than you will if you package everything together, because anyone with a brain knows they can just go and buy packaged collections of 100-200 games from an ebay wholesaler for $100-300 right now, because everyone is liquidating their PS2 inventory. If you do want to sell everything as a packaged deal then I think $125-150 is a fair price to ask for everything.
However, like I said, I would really hold on to your collection and keep enjoying your PS2 if I were you. It's the Atari 2600 of our time, and it has so many great titles that you really can't go wrong with it.
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