background: I am the only developer in a company, and I am forced to be the system administrator as well. We also have to upgrade a couple of times a year with a gun to our head. i.e. there is no possibility of delaying the upgrade.

This is what I have been doing

version 1: dev and release branch.

Before upgrade create “Version 2 Release” from “version 1 release” branch.

Once code is upgraded, generate build from “Version 2 Release” and apply to PROD.

After prod is upgraded, create “Version 2 Dev” branch from “Version 2 Release” and apply pending changesets from “Version 1 Dev” to continue working.

Do you see any problems with this? Our branch size if < 500 mb.

I prefer above approach (which is non-standard, had to learn on the job) because there is no headache of merging back the branch once code is upgraded. There is also no need to generate a build and do sanity check after merging back. Further, my earlier branch remains active in case there is any last minute code fix needed on prod.