What if you could one-click deploy to Heroku, OpenShift or AppFog? OpenShift can even have multiple competing hosting providers or you can use the free hosting from Redhat (which includes a LOT more resources than Heroku's free plan). And of course you could still do the traditional dedicated/VPS type installation.
I wasn't that familiar with Azure, but I had heard that they had Linux VMs now (which would be one option), but I did a little digging and it appears you can actually run RoR apps on the Windows side as well: