I don't know about anyone else, but much like you I look back at games I've owned/own, and I just think it's weird that they're worth so much nowadays. I also feel old, but that's another story all together.
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Disc only prices are $70-80 average and complete prices are $85-120 with a quick search of eBay completed auctions. But still, too expensive for my blood right now. I'm regretting selling mine about 7 years ago...
With that said, I think it would be great to see a remake of Metal Gear and Metal Gear 2: Solid Snake done up the standards of latest Metal Gear Solid games. They could bring David Hayter back again.
Wouldn't it always be a later date than the first version released? Assuming time always moves forward, that is.
Or maybe I'm just overanalyzing what you said?
I'd buy an HD remake of Metal Wolf Chaos in a heartbeat.
Actually, there is a prototype version with a Buck Rogers license that does it the "correct" way.
(while it might seem odd to make a '90s game with a '50s? license, it seems there was a more contemporary tie-in?)