This is one of those topics that never really gets resolved. Like a lot of things, it all comes to personal preference.
I started out with Mandrake and I am currently running Gentoo on all of my home linux pc's / servers (4 total). I like Gentoo for the fact that it doen't try to hide anything from the users unless you tell it to. I moved away from the "user" linux flavors (Mandrake, SuSE, and RedHat/ Fedora) because as I was using it, I found that "Web Browser" wasn't necessarly the web browser I wanted (one of several things that I found irritating).
Besides, I like being a little compulsive about my setups (professional hazard). I think that is one of the strengths of the different distributions; everyone can find at least one that suits them. The only way to find out whether you like it or not is to try it. If your timetable doesn't allow for playing around, then sticking with what you know is probably the best bet (although that might apply to more than just linux).
Now on to answering the question at hand. Gentoo's portage is great. I think I read that Open Embedded was inspired by Portage. Very rarley do I want to install something that isn't in portage and even then it isn't a big deal. It may be a good idea to look at
Gentoo's support forums to get a feel for it.
Just my $.02
--webslngr