files from 1991. The main file tree living in /home/win is the one I started on my first DOS machine and has been transferred to Win3.1, W98, Fedora Core, Debian, Kubuntu. Somehow, it's grown in that time from 20 megs to 200G.
I've had 2 drive crashes in that time, the first bare-metal restore was a restore from tape which blew up the first time because the Sony Superstation Windows software would not read the whole file and they no longer supported it... customer service said go to the vendor they originally bought it from and d/l a trial version. The second crash was on Debian, I simply plugged in the backup hard drive and was getting an RMA from Maxtor tech support within 10 minutes.
As for reading 1990s files, all I had to do was figure out how to use the CLI LZH format archive program jhla-utils to decompress the files. Anything I've got from then that's still usable is text files or lotus 123 (clone) spreadsheets I can open from OpenOffice Calc.