Some issues aren’t Linux problems but more like anti Linux solutions
These exist but often you can avoid them by using alternatives. I recommend not supporting LInux-hostile companies/services at all. Problem solved. This problem will continue to exist as long as Linux has low marketshare. So, the answer is not moving away from Linux, but rather to it, so that companies can’t ignore Linux users anymore. Also, using Linux has many advantages in termss of user control/agency, privacy and security.
He hates Ubuntu because he feels like Ubuntu diminishes the reasoning to get Linux in the first place
That’s nonsense, there is no “true way” to use Linux. It’s an operating system and there are distros which abstract a lot of lower level stuff away just like Windows or OS X do (e.g. Ubuntu, Mint, Fedora, OpenSuSE, …) and there are distros which don’t (or which simply don’t care about including such things) and thus are considered more “for advanced users”, where more stuff needs to be maintained/configured by hand and where less GUI-based tools are available by default. Some people actually like that sort of minimalism and the increased control, but of course it’s not for everyone.
Also, if he has trouble with the commandline usage, then it doesn’t make any sense for him NOT to use e.g. Ubuntu. Because then he obviously needs the “hand holding” of an “easier to use” distro like Ubuntu. So he shouldn’t complain about it. But this is not meant to disrespect the accomplishments of Ubuntu. The most popular OSes/distros are theones which are easier to use and which abstract a lot of things away. Because otherwise, it’d just be a distro for more tech savvy people, period. Then again, if he’s a dev he should in theory be more than tech savvy enough to use Linux as a daily driver.
Then again, he doesn’t like that 99% of apps or there like discord just don’t have a good Linux path so you have to randomly trust some potentially bad actor to keep discord updated.
I recommend using the Flatpak versions of GUI apps (in general). It’s very easy and it’s a trusted source to get tons of applications from. Although for Discord in particular, I don’t reocmmend it, I’d just use the web version tucked away in a browser (ideally sandboxed) without too many permissions on your system. Because Discord is spyware, so it’s best to keep it in check, if you need to use it. Running it in a browser automatically limits the amount of data they can gather about your system.