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What happens is that you might run into issues, you then can't address these issues with support as it isn't supported. who is then to blame? The one who asked for the problems, meaning you. Who needs to solve the issues without any support from the vendor, same answer: the one who made the decision so again you. Simply keep it all on supported level, make sure to secure it so no known security hole can be used to mess up your systems, and plan upgrades just like you do with your car. Keeping an old-timer running is expensive ;)

I agree. Only worth SQL 2012 for a lark, but it seems a lot like extra work to keep it to anything but the recommended. Of course, that time spent is better used to plan for a migration instead..

Just double check if you have Backups of the VM’s and DB (server). And if the XA boxes are physical, try to P2V them or at least P2V a few

I wanted to upgrade from day 1 but that's the upcoming item to discuss in 2022.

In my lab, I needed an XA65 server to test a script update. I had no issues with it using SQL 2019, but I wouldn't do that in prod. Well, I wouldn't use XA65 in prod anyways.