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Do they still maintain it as in, it gets bug fixes and security patches? Technically yes, bug fixes and security patches are still produced for Windows Server. I wouldn't call it a good level of effort but it exists. They are happy to take your money for such a mediocre level of effort though.

Is it Microsoft happy path? No. Microsoft STRONGLY recommends that if you are running .Net (Core), you run under Kestrel on Linux in a container. Performance under Linux is much better than Windows.

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Kestrel is more performant under Windows than Linux, but the container support isn't there
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This is incorrect, all benchmarks including those from Microsoft have proven 10%-30% performance increase under Linux.

https://aka.ms/aspnet/benchmarks

Here is Microsoft official ones, Linux beats out Windows in almost every metric.

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Do any web servers have meaningful updates? It’s pretty standard stuff. IIS can do quite a bit of the same things. It’s common in my industry. We set up URL rewrites, reverse proxys, asp.net, even node.js or python (flask) based apps using WSGI. Separate app pools for everything all on the same server sometimes. It’s never been a bottleneck because it’s pretty streamlined code. Haven't had any security issues with the web server ever. It’s nice there is a GUI but when you start looking at the configuration (xml based) a lot of the directives are familiar if you’re used to nginx.conf or httpd and with htaccess (web.config) in site directories.
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Sharepoint, Exchange webmail, and other stuff uses it... that is why it's officially NOT depricated... but man imagine having to keep up an ASP codebase today, it's not unheard of, it's just rough.
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