I agree that it's not doable to be fully comprehensive, but there are some major issues people should be aware of for each version. What might be useful is a list of major function topics and warnings next to each. For example, inline variables were introduced in 10.3 but should still be avoided as their usage breaks tooling. (32507, 33176, 33365, 22089) Another issue for those that rely on IDE Fix Pack would be a warning that's its not available for 10.4 but by 10.4.2 many features have been implemented. I remember being stuck at XE2, but I no longer recall what was broken in XE3 which preventing me from upgrading.
We are currently in the seemingly never-ending chase of requiring to use the latest version for bug fixes, but the latest version always adds new issues. We end up with developers 'stranded' at particular versions because of major issues that they are waiting to be resolved. Eventually the perceived pain of upgrading accumulates until such time as someone decides to 'abandon ship' and switch to a different solution. This thread is an example - 10.4.2 follows with even more bug fixes than the 'quality' focused release of 10.4.1 and yet, two months after release, some people cannot use the product due to internal errors. I wonder how many developers thought that their specific pain points were finally addressed and they would upgrade to 10.4.2 and then got smacked in the face with this particular issue and finally raised the white flag (especially after waiting for months now.)
For me 10.4.2 is their best release in a long while. But I'm also no longer managing complex projects with many millions of lines of code so I'm not running into this particular showstopper. However, I would really like to use inline variables, but until they fix the issues surrounding them (including the code formatter) then I refuse to use them. I assume the code formatter might be upgraded in the 10.5 release cycle and it'll take until sometime into 10.6 before it's solid so I assume inline variables are dead to me until sometime in 2023, or later. That's not intended as a slam, it's simply a reasoned forecast. Therefore it comes down to a new language feature being introduced in 2018 and forecasted to be potentially usable in 2023. Saying that out loud makes me sad and question my life choices...