[hakanderyal]

What you are asking is not really something that can be distilled into a checklist. Every product/startup has a different set of requirements, priorities, opportunities. What has worked for a company may be a recipe for disaster for another.

I remember reading on signal vs noise (basecamp blog) that they didn't hire their first server admin type employee till they've spent some months working on the servers themselves, and experiencing and learning the problem space.

What you need is experience, and it's not something that can be gained with checklist. If you don't already know what needs to be done from experience, you need to learn it by doing it. You will make mistakes, and hopefully won't repeat them again.

To lower the cost of this process, best thing you can do is find a mentor that has the knowledge that you seek. One that is willing to work with you to help you find solutions to your specific set of problems.