I used gentoo for a few years and found it to be very pleasant, with a great wiki. The only reason I ever stopped using it is because I realized how senseless it was to build everything from source on a laptop with questionable thermal characteristics. Running laptop fans full tilt for hours on end a few times a week evidently exceeds their expected duty cycle, who'd have thunk, but I had to replace the fan in my T60p twice before I learned this lesson. Building everything with Macports would have the same problem, except worse because mac laptops were never as easy to repair as thinkpads, particularly not in recent years.