Having used Ubuntu for almost exactly eight months at this point, I think I have a good idea what its strengths and weaknesses are in relation to what I want.
- It's fast at installing things.
- It's brainless to use; a monkey could install it, a monkey could keep it going.
- Packages are fairly up-to-date. You're guaranteed lots of updates at least once every six months.
- There's a big community. That has a lot of benefits; for example, if you hit a bug, the more people who share your distro, the more likely that someone else hit the same bug (and possibly fixed it).
- Ubuntu is supported by a lot of places. last.fm had a nice link to a .deb installer for their client when I needed one recently, for example. And now Dell supports it. Its hardware support is likely to be good.
- Apparently well-funded and unlikely to disappear any time soon.
- Handles uninstalling packages that were installed only as dependencies for other packages.
- I looked at how to roll your own .deb's once, and it does not appear to be something enjoyable.
- *-dev packages are not installed by default.
- Huge updates to lots of packages once every six months is not how I like to do my system upgrades.
- Installing anything that isn't in the official repos is error-prone and unenjoyable.
- Bumping the version of something in the official repos to get a new release before it appears in the official repos is non-trivial.
- The init system sucks. I don't enjoy fiddling with symlinks
- Way, way too many services are started at boot by default and it's not entirely clear what can safely be disabled.
- apt sucks. The commands are too obscure. I can never remember how to do simple things like search for a package by name or list all files a package provides. There are too many tools that are almost but not quite the same thing, or that overlap in functionality. dpkg, apt-get, apt-cache, aptitude. Its output when installing a package is unhelpful.
- The documentation for apt tends to suck also.
- Apache2 is not set up nicely. It took me forever to get Rails working.
- Too many things are considered "lib" packages and handled / named stupidly as a result. For example Ruby gems.
- Single programs are split into multiple packages non-intuitively. (Vim)
- The Ubuntu forums are ugly and mostly useless.
- Silly release names.
- Lack of cow mascot.
Given that, I think it's time to move on. Aside from the reasons above, this is largely an emotional decision because Ubuntu has been annoying me. But I have come to realize that my computer isn't for work, it's for fun. Even if something isn't the most efficient thing in the world, why not do something if it's enjoyable? Ubuntu is pretty efficient, but it's not a lot of fun in the end.
So I just finished downloading Gentoo 2007.0 install ISOs. (ISOs plural because I'm not going to use the graphical installer, so I got the minimal ISO too. I'd still like to give the graphical installer a glance though.) Why Gentoo instead of something else? It definitely has a lot of weaknesses of its own, but some strengths too. It's mostly because I'm not sure where else to go, or because picking Gentoo again is sort of like going home after being away for a while. Again largely an emotional decision. But there's nothing necessarily wrong with that. Gentoo has been fun for me at times in the past. If Gentoo becomes un-fun again I'll switch away again, maybe try something else new.
As I've said before, switching distros is easy and usually fairly safe, given a sane partition scheme and a bit of knowing what the heck you're doing. I plan to keep my /home around and wipe everything else. (I need to repartition anyways, I'm running out of room on /boot. Made it too small to begin with.) And I can always switch back if I want, or pick another distro, almost on a whim. This is one of the strengths of Linux, and I may as well take advantage.
I'm also a firm believer in keeping in mind that I can at any time be wrong about anything. I ditched Gentoo because I decided it was headed in a bad direction and it was causing me un-needed headaches. I'm prepared to re-test that conclusion and admit I was wrong if necessary. Or maybe it'll start to annoy the heck out of me again right away and I'll try to find another distro that I haven't used before, you never know. We'll see.