Things started seeming strange when the Windows signing certificate was never renewed several versions back
It's renewed when it expires - I would know since I'm the one who does that. There was an issue a few years ago where the CA revoked it when it was time to renew it, but we've since changed to a different CA.
That said however when I browse the most recent version history here:
https://bitcoin.org/en/version-history the last version listed is 22.0 which is odd because I could of sworn that release 25 was cut not too long ago.
Yes, the most recent version is 25.0. The project's website is bitcoincore.org, bitcoin.org merely mirrors the binaries. No one who works on Bitcoin Core has any control over what goes on at bitcoin.org, and although we've asked them to mirror a more recent version or stop mirroring entirely, they've been unresponsive.
I'm honestly not sure why there isn't a standard operating procedure at bitcoin core to push all the bug fixes to these earlier versions.
There is, but 0.20 is now unsupported. It takes a lot of time to backport bug fixes, especially when there are many other things going on in the codebase that make such backports non-trivial which requires additional review. There's also many things that resolve long standing issues that aren't strictly bug fixes. For example, descriptor wallets resolves many issue with watch only wallets, but its primarily a new feature that involves a significant reworking of how the wallet works. This is something that is rather difficult to backport.
Many contributors prefer to spend their time reviewing new features that overhaul components of the project which resolve long standing issues. Trying to review backports takes time away from moving forward on other significant improvements. And being an open source project, contributors are free to work on whatever they want - no one can force anyone to do anything. Ultimately there simply isn't the manpower nor willpower to backport features that also end up fixing bugs.
It would seem as though they would be behind this as it seemingly supports the ideology that plebs vote on what version of bitcoin is bitcoin based on the rules in the nodes they run. Unfortunately as it stands now I worry that with enough time people will have to upgrade their nodes less they be stuck running obsolete software rummaging through bugs and forced to upgrade to whatever version is maintained enough.
There's ongoing work to make the project more modular so that things like wallet and GUI features aren't necessarily tied to the node, but this is a large project and it will take a lot of time.