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Dude, X-Wing and TIE Fighter are DOS games. If that's all that's holding you back, just upgrade and use DOSBox to play those two games. Or get the updated versions (you can get them in a box set with X-Wing : Alliance) and you're off to the races.
Windows 98 implementation of USB is broken, only marginally better than the than the Win95 OSR 2 implementation (which barely worked). You're going to have a hard time getting it all to work smoothly that way.
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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