As someone who ran Gentoo on several boxes, including my main desktop PC, for about 15 years, and still keeps one last server on Gentoo partly because of nostalgia, the upgrading is fine only if you update everything regularly and frequently (every few days), in order not to fall too far behind.
Otherwise you get bit by dependency conflicts in your @world updates which portage cannot solve with huge list of package updates (even with "stable" branch or arch keyword) the error output is loooong and useless, and it is detective work to figure out what exactly is the problem.
In the last few years, I also had several problems with python completely breaking, leaving me without a working package manager (portage is written in python). This was always during python version upgrades (e.g. 3.10 to 3.11), which the docs docs would have you believe is as simple as changing a variable in portage configfile.
I was always able to monkeypatch portage to get it working, but it is a problem.
I like Gentoo a lot, but I think I liked it more ~ten years ago, when I had more time. If I had to reinstall my remaining Gentoo box from scratch, I'd probably use something like Debian, since it is boring and reliable.
RHEL uses a separate copy of python (called platform-python) for its most critical components, like the dnf package manager. I wonder why Gentoo doesn't do the same. Of course, it's pure bloat, but only until you're left
Python can be fast — dnf is pretty fine, and although it has no relation to package managers, my most favorite example is the kitty terminal emulator. Most of it is written in Python, but you don't feel that at all. It feels like pure C. I refused to even try it for a long time, but have been hooked for several years now.
Otherwise you get bit by dependency conflicts in your @world updates which portage cannot solve with huge list of package updates (even with "stable" branch or arch keyword) the error output is loooong and useless, and it is detective work to figure out what exactly is the problem.
In the last few years, I also had several problems with python completely breaking, leaving me without a working package manager (portage is written in python). This was always during python version upgrades (e.g. 3.10 to 3.11), which the docs docs would have you believe is as simple as changing a variable in portage configfile.
I was always able to monkeypatch portage to get it working, but it is a problem.
I like Gentoo a lot, but I think I liked it more ~ten years ago, when I had more time. If I had to reinstall my remaining Gentoo box from scratch, I'd probably use something like Debian, since it is boring and reliable.