NOW 34! (Now thats what I call Gentoo!)
So people have been commenting lately about Gentoo. I respect these people, yet I also fear them. We have a new council; they are better than the old one already (after just 1 meeting!). The council is full of doers. Many of the last set were not doers. This is an improvement
The Philosophy of Gentoo
Every user has work they need to do. The goal of Gentoo is to design tools and systems that allow a user to do that work as pleasantly and efficiently as possible, as they see fit. Our tools should be a joy to use, and should help the user to appreciate the richness of the Linux and free software community, and the flexibility of free software. This is only possible when the tool is designed to reflect and transmit the will of the user, and leave the possibilities open as to the final form of the raw materials (the source code.) If the tool forces the user to do things a particular way, then the tool is working against, rather than for, the user. We have all experienced situations where tools seem to be imposing their respective wills on us. This is backwards, and contrary to the Gentoo philosophy.
Daniel Robbins
Previous Chief Architect
Do the tools Gentoo produces work for you, or against you? They work against me and it bugs me quite a bit. Especially portage with all it’s shortcomings; but other tools as well. Webapp-config is getting better (as is layman). eselect depends on the module; etc-update is crap (but has replacments). Quickpkg is horrid but portage-utils rocks out over equery. What tools piss you off? What tools are working?
Gentoo is supposed to be an intuitive system for “making my own gentoo.” It no longer is. I can’t build KDE the way I want because it just stops building. Giving users a choice is pointless if that choice is always broken (No Flameeyes; I’m not trying to bash you or KDE here). Every piece of complex software has these issues; PHP had it last year and it was only quasi solved. Any attempt to deviate from the “normal” USE flags often fails.
This was the case for the stage1 install and it was canned due to an inability to support people doing dumb things. When will “trying to use PHP in a certain configuration” be equal to “doing dumb things with PHP”. Will PHP get cut as well (again; not a jab at the PHP folks; more of a conjecture).
If we get pkgcore or paludis; what will happen with USE and slot dependencies. They better represent the complexity that is inherint in the problem of building packages from source. Will this new representation even help? What if the complexity is too much to handle in a sane manner?
Obviously QA has problems (they can’t test all 5.5 * 10 ^ 57th combinations of php USE flags); so what will they do to address these issues? While choice is important; too much choice is also too much work.
Once again I ask; where is the middle ground?

File a bug about your problem, please.
The one thing that really annoys me is etc-update. I’m impressed with how many things in gentoo were designed to solve complex issues (java-config among others), but etc-update hasn’t changed one bit (as far as I know), since v1.4, and it’s still horrid. What separates gentoo from “the rest” is how convenient and pleasant the command line tools are (good readability with color output, lots of helpful hints etc). And this is where etc-update is seriously lacking, I think it’s a shame that new users are exposed to it, it should be replaced. I’ve been using dispatch-conf and while it’s better, I’m not too thrilled with that either. gentoo should have a much better out-of-the-box tool for this.
I think the tools are pretty good for a desktop user. As a developer, however, they drive me absolutely insane. I find that when I need information about a herd, an ebuild, an eclass, a changelog, etc, I have to use completely different tools for each one. Not only that but there are so many tools out there that I’ve never heard of, that everytime I start whining about what is hard to do, someone inevitably tells me just to use foo-util as if I should have known about it already.
Hmm … maybe I should write up some portage utilities index page. That’d help, at least.