Gentoo does take some getting used to, but an "emerge -C packagename" isn't that bad. You just do an "emerge -pv depclean" afterwards to see what it wants to remove, and then "emerge depclean" do remove any unwanted packages that the one you removed depended on.
I have been using Gentoo for about a year, and I haven't run into anything I couldn't fix yet. I run completely ~x86 (unstable, well, unstable ebuilds, not unstable packages).
I do agree though, if you don't enjoy using a source based distro, Debian is the way to go. If I were to use a binary distro, it would be Debian.
It is the same with most distros though, once you learn the directory structure and the package management that each one uses, nothing is really that hard. I like the hands on feel with Gentoo and Debian. Gentoo takes a while to learn, but once you do, it is so easy it is like any other distro. I am still learning on Gentoo, but I just like it. Plus, the forums are a big plus no matter what distro you use.
bersl2, if you feel that uncomfortable upgrading a package on Gentoo, you can use the quickpkg tool in "gentoolkit" to make a backup of the program you are upgrading before you upgrade. Then, if the upgrade doesn't work, just mask the upgrade, and emerge the package you made to revert back without having to recompile. If the package you want to upgrade can be slotted, then there is no reason to package it, just switch back to the previous version and remove the other because if it is slotted, it will install both alongside each other.
In the end it comes down to personal preference and what you are comfortable with. I am comfortable with Gentoo, you are comfortable with Debian. They both do essentially the same thing. It just wouldn't be right without choice.