Do you know of a case study that details the necessary steps, possible issues, and cost to migrate on-premise server software to infrastructure clouds such as Amazon EC2 or MS Azure? Or do you have experiences in doing it?
Something that would help to answer questions like: Under which circumstances does it make sense to migrate a web-application +DB hosted on 5 dedicated servers to EC2?
I would counsel a move to EC2 in the following cases:
1. You need the ability to run a large pool of additional servers on short notice. Say you do something computationally expensive and fairly time-sensitive, and need a big burst capacity.
2. You want to be able to set up and tear down numerous staging and testing environments.
I'm sure other commenters can add to this list. My generic advice is, stay out of the cloud unless you know you need it. It's expensive and setting it up is a time sink.