Thank you for sharing your story!
For your kind of use case and issues, I’d recommend finding someone local with a good amount of Linux experience and do a couple of pair sessions. I find this transports a lot more (especially ‘soft’) knowledge on concepts and how to do things efficiently. Also, it helps to share frustrations ;-)
Linux does not try to be another Windows. While it’s fairly possible to treat it kinda as such especially in newer times, it won’t feel efficient or convenient that way, in my experience.
I’d guess about monthly to bimonthly, in the sense of submitting a fix for an issue that affects/concerns me/my use of open source projects.