I feel there is a balance to be struck between a project that is popular (where if you run into problems, you will get good support), and one that technically gives longer-term support (but if things go wrong, that support might not be very good).

I haven't used a lot of different distros, but for me, Debian has been a good balance of those factors. You may need to do more upgrades per decade, but the ones that you do are more liable to go smoothly.

Just my 2¢ on the topic (:

I don't work on a server team, but in network/network security. My company made an announcement that they are extending our product's software lifetime to four years: 3 years standard support + 1 year high sev patches.

It seems to me in the 2020s that 5-7 years is plenty of support for a single OS release, and that OS support teams should be nimble enough to roll out new instances and migrate data at that cadence.

So there is a project that you care enough about to keep it alive, but 1-2 hours every FOUR YEARS is too much? At some point I just have to call you lazy dude.

Either the 1-2 hours is a drop in the bucket compared to what you spend on it anyway (like a blog you still regularly update), or you don't actively update the project but still care enough about it to spend half an evening every few years, or you should just admit you don't care about it enough anymore to do even that. In the last case just delete the project.