Actually with the kind of knowledge and background you've displayed in the forum, Gentoo wouldn't be difficult at all.Gentoo seems like something I'd like to try. But not yet, not by far -- it sounds way too complex.
The documentation takes you step by step explaining what's going on. Actually you learn a lot, but as MU pointed out, you have to read a lot too. I understood a lot of Linux concepts by trying Gentoo. I would not use it as my primary system though, but I think that Its quite a fast way to understand the posibilities.