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Insomniac, ouch!
I will only sell games I didn't enjoy and weren't already part of a series of games, like Pokemon, Final Fantasy, Fire Emblem, etc.
As for if/when they are worth a lot of money, I think that's even more reason to keep it in my collection.
Unfortunately, when I was younger, the Sega and then the PS1 belonged to the family, as did the games, so I had to share with my brother and sister, and a couple of years ago my brother sold a lot of the older games we ha without consulting anyone... :/
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