I know you've probably written off gentoo at this point, here's a completely random bit of usage advice:
- Set use flags as you need them, even if this means re-installing the same thing multiple times. This avoids big important packages being pulled in as mere dependencies (though you can add them to the world list afterwards) and more importantly lets you set up and configure everything one at a time and makes it more likely that you'll notice error messages.
- Don't be afraid of package.keywords, especially for very specific use flags.
- Avoid gnome if possible. I don't know wtf it is with gnome, but it seems to be the poster child for weird and hard to diagnose issues as well as crazy dependency trees.
- Pay attention to what virtual packages are doing. Usually they are in your best interest, but not always.
- Don't bother using ebuilds for web apps
I started using a Gentoo derivative (Sabayon*) about a year ago, and it's an absolute pleasure to work with. (Particularly how colourful the package manager is compared to Debian.) In addition to the above, I suggest the following:
-Keep package.use, etc. and make.conf under version control. (This is really helpful in case you accidentally break something.)
-Use git instead of rsync for the portage tree - it's much faster, especially when the total no. of changes is small. (This is doubly true if you have multiple Gentoo installs.)
* Sabayon has systemd as the default, but it's easy enough to change back to OpenRC and being able to use binary packages saves a lot of time.