The old version of Microsoft Flight, that I spent like $100 on additional content for, stopped working because it relied on "Games for Windows Live" servers that Microsoft no longer runs. I spent about 5+ hours on different support calls trying to figure out a workaround, but to no avail.

The sad truth is that any company that uses DRM couldn't care less about you. They only care about money and they won't even push an update to remove DRM for a game they don't even sell anymore, so that people who paid money for the content can actually use said content.

Another instance where pirated games provide a better experience.

Are these instances getting more common or am I just more aware of them?

Denuvo, the lolcow of gaming.

While it should probably be legally required to release unlocked versions at least after the end of support (could have the side effect of longer support!), cracking software is at least (AFAIK, please correct me!) generally legal for compatibility purposes.