Windows Server has been painless for me. We use MSSQL Server which is a good database, much better than your MySQL. We use PHP, ASP and ASP.NET in no particula

Windows Server has been painless for me. We use MSSQL Server which is a good database, much better than your MySQL. We use PHP, ASP and ASP.NET in no particular order. I prefer PHP and use PHP. It works flawlessly in IIS. Also, the subversion server is very easy to manage (tortoiseSVN to create repositories, etc). However, for email, Linux is much better. Email hosting in Windows sucks. MS wants you to buy Exchange. This is my experience with a dedicated Windows box. Shared hosting in a Windows machine is the world of pain other posts describe.