A word on Windows updates, just as an example. My son has an MPIO DMG MP3 player, which worked fine. When XP Service pack 2 came out, it could no longer link to upload and download files, because the changes in security stopped the thing working. Eventually, the manufacturer brought out a new driver and everything worked fine again ... until quite recently when new Microsoft hotfixes came out and it doesn't work again.

As I say, this is just an example, but be aware that any updates could have similar effects on other equipment you own (digital cameras, etc)