>I went through this about a half a year ago and I checked out a bunch of cloud services. I was in the same boat as you with a server 2008 R2 machine. The machine's perf was fine for what I needed but at 6 years old there started to be a few hardware issues (one of the backup drives failed and occasionally the box just wouldn't come back from a restart).
I have been reading through that message and it is really great.
I was curious to know about your backend database. Is this SQL Server? If yes, have you installed a version of your own or you are going through SPLA?