What you need to understand (at any given point in time) is: - how is the complexity & scale of your system going? Make projections - identify potential break

What you need to understand (at any given point in time) is: - how is the complexity & scale of your system going? Make projections - identify potential breaking points in this - figure out roughly how long it'd take to migrate to e.g. AWS - the cost of migration (not only the diff between your current costs and AWS costs, but the opportunity costs all the projects you won't do while you're migrating) - now you have your "buffer" figured out, as in, when you need to start acting.