Feline,
You seem to have a good handle on PCs. I would think of getting 512Mb of RAM for your comp and installing WinXP. Once you go to WinXP, you will not go back to Win9X and you will kick yourself for not upgrading sooner.
There are some good OEM deals out there that almost get it down to the price that would make it a stocking stuffer you could ask Santa for. (Do not forget to ask Santa for the RAM too.)
Take Care,
Richard