Comment by gerdesj

"But despite my best intentions I have not mastered it - in fact I barely feel like I understand it. When I remember to update it a couple times a week everything is pretty smooth. Go much longer than that and all bets are off. ... I just don't have the discipline to keep up."

You are so close to enlightenment! When you can repair a broken Gentoo box (which is its default state), whilst still providing service, you are a man my son (pronoun assumption - soz!)

I do run Arch on all my personal stuff these days (DebIan n Ubuntu at work and others as required) but Gentoo was my first real love and it taught me to never fear a completely broken Linux box. Provided the broken bit is not screwed hardware then Gentoo can survive nearly anything.

I have a box - a VM running on esxi in my attic that got a bit behind. By bit, I mean 2013ish - I've just checked out /etc/kernels to get an idea. You can use git to make /usr/portage go back in time and then gradually update your box to now. It's not something that I recommend for the impatient but you can do it. The worst bit was dealing with things like Let's Encrypt CA changes and finding old packages. I often had to download them manually and slap them in the right place.

You complain about compilation times but back in the day I had a laptop that I left running on a glass table for over a week (worried about heat) cranking through what would eventually become @world. From memory, it was for the GCC 3 -> 4 upgrade and the advice at the time was compile everything until your eyes bleed and then do it again. Nowadays an ABI change is handled rather better and with better advice.

The Gentoo wiki is a very decent repository of info (I wrote some of it, and probably ought to revisit and update my offerings).

The contrast with other approaches to software is striking when it comes to docs n that. I've recently "solved" an MS Outlook MAPI to Exchange snag that might have been easier to diagnose if I had access to the source or logs that weren't solely designed for people with access to source code.

Do stick with it and do ask for help. You are very close ...