As someone who contributes to linux's printing subsystem I will say that we put a lot of effort into keeping old printers working. To the point where the original apple laser printers should be usable. Provided at some point it worked under linux then it should still work. Every time we rewrite the printing system we bring along all our supported printers through some comparability method.
On the other hand Microsoft and printer vendors do drop support for some printers at every major windows revision. Please do give Ubuntu a try.
I had tried SUSE Linux as a replacement, and had to go back to Windows, but the latest versions of Ubuntu sound like they are very good.
However, the cost of additional trips to my parents', grandparents', or uncle's houses for maintenance or unfamiliarity is still too much for me, so I'm still reluctant to recommend it to them (especially since their computers already came with Windows preinstalled).
I will try it out for business use as well if I finally start my own company (hopefully next year).
Edit: thank you for contributing to Linux and I hope you will be rewarded for it.
Edit2: I have great faith that the newer generations will be much more likely to try out and like Ubuntu, since they've been given the OLPC computers :) . While I'm reluctant to suggest my older family members to switch, the younger ones have a chance.
On the other hand Microsoft and printer vendors do drop support for some printers at every major windows revision. Please do give Ubuntu a try.