@rathel I don't use qtile, but it looks like Gentoo has an older version than Arch (0.17.0 as opposed to 0.21.0), so maybe your config relies on something that isn't in this version. That's my best guess at why it's not working.
And portage definitely takes a bit to get used to, but it's definitely worth it imo.
@rathel Sounds weird that the pip version didn't even start. Not sure what the issue there is. Awesomewm is pretty nice tho.
If you're tracking stable, you can sometimes get newer versions of packages by adding the package atom to /etc/portage/package.accept_keywords (to let you get the testing version) or you can track testing overall (I forget how because I track stable). This won't help for qtile right now, but it might help for some packages. Otherwise, probably ebuild writing time lol.