We are starting out small and working up to a very robust model, region intensive and then rollout. Are the versions interchangeable, data coherent and seamless or do we have we to re install data on upgrade.
If you're working with a child theme it will make upgrading a lot easier in terms of not losing your changes, otherwise you would find the process a lot more tedious if you have customized the theme. You don't need to reconfigure settings when upgrading though.