First of, I'm a BIG fan of Linux servers!
But despite that, I'd really take a Windows box in your case.
Updating the webserver, PHP, MySQL server and what not indeed is way more easy on Windows IMO.
In case of PHP you just replace the PHP.EXE and that's it.
For the other, run the installers and you're done.
I hate the need to compile everything myself on a linux box.
Maybe I just looked at the wrong places so far, but IMHO Windows is way more easy to mantain....
And if you spend some of your safed time it can be as performing and secure as a Linux box....
[EDIT]
What's the $1500 about?
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