Well, Amazing Charts 6 stopped working with Windows 2000. Dangnabit, I actually had one of those as a backup machine (had an old immunization program that we occasionally queried) and also in a pinch as a remote desktop.
That was quite a few years after 2K stopped being supported. Shame on AC for not continuing to make sure it was compatible! I converted it to a VM, updated it to XP and the immunization program stopped working. We now run the VM when we need to query the program.
I've only had that machine for 10 years, IT SHOULD STILL BE GOOD. Shame on Dell and Microsoft for planned obsolescence. My Pentium II 400 was every bit as fast as a Pentium 4 2.8 with Windows XP. Oh well, guess I really needed to use the Meaningful use money.