Before you install an OS be aware of the limitations of accessing low level hardware directly. From Win2000 on most hardware can't be accessed directly unless you want to write a device driver. So if you want to program the parallel port, use something like Win98 or you will need to get a 3rd party utility to allow access to LPT1 (the parallel port).

For my Win2000 machines I use the trial version of NTPort (http://www.zealsoftstudio.com/ntport/index.html. The only reason why I'm suggesting this is because I have used it and I know it works.

Happy days in Win98/DOS though, real easy to quickly write some I/O stuff in QBasic

Also my favourite resource for interfacing the parallel port is: http://retired.beyondlogic.org/spp/parallel.htm. Retired!