I fully agree that working with Gentoo is no fun at all, as Julian points out in his post
My impression, when I tried Gentoo for the first (and last) time is the same. Thats not because it is made bad. In fact things in Gentoo aren’t made that bad. There is good documentation, portage is quiet nice (with its USE flags and alike), but in the end I’m not really satisfied.
After all Gentoo uses a copied concept, which itself is good. The concept is derived from the BSD-world and is just the concept of source-based systems. This concept has its advantages over binary distributions, because it allows a flexibility that is not really possible with a binary distribution. That really is the only appreciable advantage of these systems. Users of these systems (including FreeBSD and alike) tend to give other arguments as well: Newest Software, Highest Performance and even Security is a point they give.
Usually the „newest software“ argument is brought up with a rant against Debian. I keep hearing statements like „Debian Etch is totally outdated and Testing is broken“. That statement in itself is just wrong, but the important thing is: What do you need such new software for? On a server its preferrable not to upgrade to each and every major release, for certain reasons. Its also a bad thing to build on production systems, so you need to take further measures to administer systems like that. On a desktop I can understand the logic, but then again: No. Why would I want a system I have to compile from scratch and on each upgrade (wasting a lot of time, power etc.) which changes often?
The performance argument is the dumbest of all. Binary distributions usually build binaries for various platforms. And while they can’t be optimized for a very specific processor or a very specific feature set (=reduces binary size) they usually perform well enough that a difference between the self-compiled Gentoo system and a foreign-compiled Debian is not noticed by the user and sometimes not even measurable. So the time you save during the lifetime of your builds (which is not very long on a Desktop, is it?) because of the enhanced performance is used up a hundred times, by the time you waste for compiling the whole software only for yourself. Even if some of the software performs noticable better (e.g. video processing is said to benefit a lot from an optimized platform).
What about the security argument? It has been said, that you get your updates earlier then users of binary distributions. That is partly true, because in a binary distribution the update needs to be built first, before it gets to the end user (however, everything before is the same for a binary or a source distribution). But do you really follow security issues that close, that you benefit a lot from this? If you do, indeed, you save some hours. If (and only if) both distributions have a solution for a security issue at the same time.
Anyway. The flexibility argument can’t get discussed away. Its the argument that makes Ports in BSD-systems attractive. You can have exactly the features you want, with the build-time options you want. In a comfortable manner. That is in contrast to binary distributions where we package developers need to guess which features might be needed (/wanted) by the users with mixed results. Good if they can decide for themselves. Still, I don’t see the reason for compiling the whole system, if I need one or two customized components. So I go with Debian and customize packages if I really need/want to. The only difference is that it takes a lot of more effort.
I would love to see something done in Debian to reach a compromise. Making rebuilding of packages with different options very comfortable. We have DEB_BUILD_OPTIONS, maybe we should enhance it to support a lot more options then noopt,nostrip or nodoc. Possibly it would be a good thing to standardize on some use flags (e.g. [no]ssl, [no]ldap, etc.) and support them in the debian/rules file. This way building customized packages would be as easy as setting sensible DEB_BUILD_OPTIONS and run dpkg-buildpackage on the source. This could be eased further by providing a tool to download the source and build a given package (IIRC such a tool already exists). How does that sound?