Not evangelizing in any way, but it is worth a try. If “back in college” was 10 years ago, I could hardly agree more that it was pain all around, but it is so much easier nowadays that even I without any advanced knowledge in Linux I could setup one of the harder distress (Arch) without any pain at all (thanks Archinstall).
Understandable, from a software engineer’s view, I get it.
IMO the biggest challenge is to fundamentally change how one thinks about given system. The goal is not to want to get it to behave like windows. But I understand it is hard for someone who used windows his whole life (I’ve been like that aswell). LibreOffice will never look like Office, downloading new software is not gonna be just running an .exe installer, and system settings will sometimes not be just “click here and it does what you want”.
Not trying to convince you (or anyone), but just my two cents.