I have had some similar error messages while trying to upgrade from 2021.1.4 to 2023.2.3… no perfect solution yet to get me all the way to the newest version, but I’ve found that for whatever reason v2022.1.0 will at least start the experiment. I’d be curious if it works for you too.
Even though 2022.1.0 works for the most part, there are some idiosyncrasies, like some objects being displaced relative to their original location (Moved to top or top right of screen) and the mouse component is pretty unusable on a Mac locally. In addition, with the change of python version, you may want to look at any code components you have to make sure they are still behaving as expected.