I think you should look at it more from a broader paintbrush than at the web server level.
Think about what services you are going to offer and if the framework is there to get your work done. This also takes some careful planning on your part to try to sense where things are going to be in the next 3-5 years out. What you write today will be an investment too...
I ran into the same delimna as you did but had to step back from my Windows development experience and biases. I eventually headed into developing on WinNT+Apache+mySQL+PHP. My issues are mainly licensing/costs. You cannot beat Apache/mySQL/PHP being free. I plan on replacing WinNT with Linux or FreeBSD as my preferred operating system. But for now, since PHP is totally platform independent and so is mySQL, it's not an issue for me presently.
Linux + Apache, J2EE using JSP, Un*x variants + ChiliSoft, Perl/CGI, Microsoft .NET are all other alternatives too.
Kerry Kobashi
Kobashi Computing
