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I tend to restart games often, which makes me wish it was easier to keep copies of old save files. Just so I could have a record of each time that I played through the game to see how much of my life has gone into it.
This is also why I tend to get multiple copies of the games. So I can restart them easier without losing everything.
I've played the first generation over many times. I have now memorized almost every route and city layout.
I restart most of my games once I've beaten it and if I have somewhere else to send my Pokemon to so I don't lose them. I often don't play the game all the way through again, unless I have to.