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I started on Windows 98 with a computer that was given to me that I had to upgrade with a couple of friends' help, just so it could barely run it. My HDD was too small at the time to accommodate storing another copy, I think. But I learned some things and at least the knowledge that I wouldn't have to get a new computer when the OS crashed and burned!
Fortunately my one friend knew how to do a manual registry restoration to get it to boot a couple of times, which helped in some cases.
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