I could write a really long post with lots of personal viewpoints.. However, I think it's summed up best by saying two things.

a) The market will drive both oss and private development in a direction that suites the needs of the time..  So whether there is a market for IIS + ISAPI.dll + Mono I can't comment as I haven't seen any data..
b) One of the beauties behind oss is that if you don't like it.. You always have chance to make it better..

I find Mono to do almost exactly what I need and quite well at that.. For the parts that maybe are insufficient right now I'm choosing to work around it and make it better as best I can or simply wait..

While Apache may have a majority market share with Linux I'd say it's certainly not the only web server available..  If you really need Mono + some other web server then I'd say look at building your own modules as it's certainly possible and you even have the source to a working one currently..

Zeus (commercial)
Lighttpd (oss)
Tux (oss set of patches for kernel)

There are others, but this is what comes to mind

Good luck!

C.
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