This is a fantastic question. I'm curious to hear what other users think about / contribute.
Unfortunately, I don't know that there is a static list of things to check / ensure. A few items that might be worth keeping an eye on:
- RStudio should be reinstalled
- many R-focused system dependencies will need to be reinstalled (as you highlight)
- I would expect that the version of R and many of the R packages will need to be reinstalled
- This article has some interesting information about compatibility of R packages across R versions. I would expect similar cryptic issues with changing OS version: https://rpubs.com/wch/275466
As a result of these issues, and especially because you are using docker, I generally like to think about this process as not so much "upgrading the OS" but migrating from one OS to another. I.e. the only thing that should stay between versions is the data directory / home directories where code and other related files are written.
My approach would be: test, test, and test again. Another benefit of using docker