I know the current release is 2.4.2 but I want recommends based which of the versions is less problematic currently. You know that experience: you install a version and one thing or the other fail - resource tree missing, extras not installing, installed extras not working, TVs not working, etc. I've been away for a while. TIA.
Server configurations, browser issues and in some cases hiccups during upgrades can cause the issues you mention on what are actually very rare occasions.
Personally, I prefer to go get the latest 2.x version from github and build it myself, but I can certainly understand where that might not be appropriate for building a live site.
In my experience, almost all of the significant problems that happen with MODX upgrades are due stuff in the MODX cache or the browser cache and/or cookies. They almost never affect the front end of the site.
I've had *way* fewer issues since I started using the UpgradeMODX extra, which manually deletes the files in the core/cache directory on every install.
There's been a lot of changes since 2.0.X including new db tables and what not, so I'd strongly advise going for a more incremental approach. You should be able to go from 2.0.A to 2.0.Z without an issue since these are just patch releases, but when new features are introduced, such as in 2.1.X, 2.2.X, and so on, you should tread with extra caution.
When upgrading, also be sure to update your extras. Some extras are know to be buggy in the latest versions of MODX.