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I would say take a holistic view. For example, let's say that as part of your disaster recovery (DR) strategy, you are running applications in the cloud in the event of an outage. Once you get a little bit of familiarity with this process, you should take a step back and decide what the cloud-based DR environment should look like.
Rather than just doing disaster recovery of the workloads, applications and servers you have running on site, you might want to think about the next few years. What should live permanently in the cloud? What should remain a hybrid, where primary data is on site and secondary data is located in the cloud? What will never touch the cloud?
It's important to understand the infrastructure and how much workload is associated with each of the above data sets. Then you can start to decide what fits where based on the volume you will have over several years, rather than just one-off applications.
You're likely to get a better discount -- and probably more assistance and cooperation from a cloud provider -- if you can come to them with a plan that says, "We're going to move this much into the cloud over a period of a year or two."
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