Zac,

Take a look at this: http://technet.microsoft.com/en-us/l...(v=ws.10).aspx
You may have already seen this document but I offer it in case you haven't.

I know it is basic but for the most part 80% of our upgrades happen without an issue. However, we do run into a custom script that will cause a problem from time to time. We just have to figure it out when we find one.

The biggest protection, as you already know, is to setup that dev server "as is" and test it from there. I wish everyone would do that but we will have clients that forget to test an upgrade or change on a dev server ( or cloud ).

If you run into any specific issues drop me a note and I'll run it past our window server gurus.

Steven