Even before you can afford a part-time DevOps engineer I highly recommend automating your system administration as much as possible. When you say you should script your installation of an application server I recommend doing that with Chef!
This will allow you to quickly bring instances online on about any cloud. HP, AWS, Linode, or your own self-brewed OpenStack cloud. You will still have challenges with your persistent data but it's a lot easier to breathe and act quickly with your persistent data knowing you'll have content servers to access that resource.
edit: I have no affiliation with Opscode - we aren't even a paying customer we use their free server. I am sure Puppet or any system administration tool will get you similar milage.