Forum OpenACS Q&A: Response to Windows, AOLServer, and OACS
The *best* solution, from a marketing perspective, would be IIS. Windows shops like Windows products. If they're MSCE, then they've probably been taught how to "secure" that server, how it's better than the others, how to upgrade it, etc. However, trying to kludge the OACS into IIS would be painful.
Apache 2 has been built from the ground to be portable. The Apache Portable Runtime is a foundation layer which was developed to provide cross-platform deployment. From the benchmarks that I've heard about, it even outperforms IIS on a Windows box. Apache 2 has made really great strides in becoming a much better application and much less "patchy".
That being said, OACS uses the features in AOLserver extremely heavily. mod_nsd is basically a mimic of these features. Rob Mayoff, a wizard level AOLserver hacker, built the original mod_aolserver. Even then, I've never gotten the sense that it was anything other than a quick hack. There's *a lot* in AOLserver that would be really difficult to reproduce.
IMO, the best part of the OACS stack is AOLserver. So I'm probably not the right person to ask how it should be replaced, and I'm certainly not qualified to say which would be easier, getting AOLserver to work on Windows or to build mod_nsd into Apache 2.
But I think it would be a much bigger win to have mod_nsd as then people in the Unix world could take advantage of it as well.
As far as my comment about running cygwin, I think it will be distasteful to a Windows shop to run anything in Cygwin. From my experience trying to sell to Windows shops, they want native Windows apps.
Just imagine trying to get Linux shops to run Windows products under WINE. And then realize that Windows admins are usually far less experienced and qualified. IMO, it would be a disaster.