As for how everything runs today, you would need identify what information you need that would impact migrating. It's just seems too broad at this point - unknown versions, package storage and usage, how you plan to upgrade reports, hardware/OS changes, etc.
In terms of deployment settings, that seems like something you need to figure out based upon what and how you deploy based on business needs, versions. There are hundreds of questions you need to ask the business. Maybe sit down and come up with all the questions to ask the business and come up with a list of things you need to know about each component and work on your scripts from there. 

Sue