As an insane Gentoo user, sign me the F*** up
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I have a VM that was rather unloved that I ended up using git to go back in time to gradually move it forwards in time and update. It took quite a while. It started off life in the noughties and now sports a 6.10 kernel. I won't bore you further but it did take a while but the data is still there and accessible on a modern platform.
What is mad about that?
emerge --update --deep --with-bdeps=y --newuse @world
There is a lot of very decent technology in Gentoo - it literally describes what all other distros need to do, in some cases.
You mention a week of compilation - I remember the gcc 4 thing too!