Hiding ancient alpha or beta releases or versions that have been long superceded would be a nice start indeed. It could be even up to the author to define what a "beta release" is. Although I don't think that proliferation of old or duplicate versions is really serious at the moment. It's a real problem, but not really one I think is that big of a deal. It could be worse.
I see now the problem that manual curation needs a curator … Yeah, that's a problem indeed.

Especially if those people disappear.
I wonder how content manages to get into the content system … Does it need an approval from anyone? Or can everyone just post an add-on and it instantly appears for everyone? I mean, is there any verification required?
I am still not convinced the star rating system is going to cut it. You have basically mentioned all the problems with star ratings yourself. All reasons why I am skeptical.

It's not a great solution.
Re-uploading carries the risk of licence violation for non-GPL or non-CC stuff, and of course worsens the problem of "now there are two versions of this AI, which should I use?" facing new players.
Well, since OpenTTD promotes non-free software I'd say that's kind of a self-inflicted wound then. The solution, of course, is “boycott all proprietary content”.

Also note that not even all CC'd content is really free/libre, there is sometimes the awful "NoDerivs" or "NonCommercial" clause which is incompatible with free software licensing. Yeah, I think just let those add-ons rot. They don't deserve support from the FOSS community.
Talking about automation: Some kind of automatic testing
would be really great. I mean, I do know that community AIs have many bugs, but I can't really put my finger on where
exactly the bugs lie. Automating the testing away, even just partially, would probably help a ton finding all those "hidden" bugs. But I admit I have no idea how exactly that would work in practice. I'm not sure if even a dedicated server is really required to do with. On the other hand, where are all those donations going to, anyway?
Hmmm, I am out of ideas right now. To be honest, I can't really think of a great solution on how to solve this once and for all.

Curation was my main point here, but if that's not possible, I guess we're doomed.
Maybe the only path forward here is give up on the problem altogether and write a big fat notice that every add-on you see might be completely broken and that the OpenTTD team takes no responsibility whatsoever.
What do you think about taking/forking SimpleAI and turning it to the "official default AI"? Heck, even if SimpleAI is included into official OpenTTD
verbatim (except renaming it to something like "DefaultAI"), that would already be a huge win. I think SimpleAI is "good enough" for now. It's closest to TTD behavior, it builds the basic things OK enough, it's GPLv2'ed. The only downside for now is that it doesn't support ships. But that's still so much better than nothing.
I think the simple act of adding
any default AI would be a massive improvement of OpenTTD that cannot be understated. Not really because SimpleAI is that great, but because it would be the first time in years since OpenTTD shipped with an AI (the last time was in 0.7, I guess, i.e. ages ago). So in ther words, the day OpenTTD adds a default AI would be historic. xD