Sean Costain, MSP from Australia moved his server from WS 2003 to WS 2008 with a lot of problems!!! (kidding). It looks like the process was a breeze as he posted in his blog
Full installation, clean, simple, fast, controlled.Web server, IIS included and more.
Not all the MSPs are code lovers, there are a lot of them with great IT skills and experience.
And off course you can get the bits in DreamSpark