The Win9x/ME OS from Microsoft was notable for much more frequent crashing and the "blue screen of death" fault, which really isn't dependent upon one's computer knowledge or tech savvy. System reliability is worth the upward migration to Windows NT workstation, Windows 2000, XP or a flavor of Linux. Couple that with the diminishing support of manufacturers to develop backward compatible periperhal drivers for new equipment, then it's clear that an OS upgrade will breath new life into old hardware that is capable of running it, which would be the majority of Pentium II or better based PC's with a good amount of ram.