I use Gentoo on a few of my servers and I've had a love/hate relationship with it for quite a while.

The thing I really like about Gentoo is that it makes maintaining custom packages fairly simple. Compared to a binary distro like Fedora, maintaining modified versions of software is a snap.

On Fedora, I download the src.rpm, unpack it, edit the .spec file, repackage it and install it. It's not a huge deal, but more unwieldy than it needs to be. What really concerns me about doing this is that, like most administrators, I like to keep my updates pretty automatic and worry-free. Having to take manual steps means that I'm more likely to forget that say, PHP needs to have mcrypt support compiled in for some application only to see someone's site go down after an upgrade.

In contrast, on Gentoo I just set a flag in a single file and I'm pretty much done.

I also like the fact that there are no major versions of Gentoo. With Fedora, I can expect to have major downtime at least every year or so when a new release comes out. With Gentoo it's a gentle upward slope (well, not really, but I'm getting to that).

So what's to not like then? Well, I think the problem comes down to this: when I'm working on my servers, I'm in administrator mode. That is, I want to deal with things like service configuration and whatnot. Also, in administrator mode, I'm usually dealing with time-constraints and concern over uptime. The problem Gentoo presents to me, as an administrator, is that it makes me concerned about non-adminstrator things, like the build tool chain. I'm not aware of any other distro that can so easily destroy your build tools after a simple update as Gentoo. When has Fedora ever told me that GCC can't create executables? Never. On Gentoo? It's not quite a regular occurrance, but still way too frequent. Each time I end up spending an hour on Google and Gentoo forums tracking down the solution while the server is as useful as a 500 watt brick.

To boil it down to one line: it makes me, as an administrator, worry about things that are the realm of programmers.

Now, I am actually a programmer, so you might think this is a silly complaint. It would be except for my other two concerns as an administrator: time-constraints and uptime. As a programmer, if my tool chain gets hosed, I'll take my sweet time figuring it out. I develop on a standalone PC, so uptime is no concern. As an admin I don't have this luxury. For the same reasons I don't develop on live servers, I find Gentoo to be a suboptimal choice for live servers. Basically, by running Gentoo, you've made the server into a development machine. Worse, it's someone else's development machine.

Now, in all fairness, the approaches Fedora and Gentoo take are very different and it seems quite likely breaking the toolchain after a GCC/libc upgrade is inevitable (I've been told that SourceMage doesn't have this issue, but I don't know from firsthand experience), but understanding and even excusing a problem doesn't make my problem go away.

These sort of issues make the "gentle upward slope" of Gentoo not so gentle. While I may not have two hours of guaranteed downtime because a major release came out, there will be downtime, only it's not planned-for downtime. It usually happens when you least expect it. With Fedora, I know I'm about to do a major upgrade and can schedule it accordingly. With Gentoo, I'll only know if I religiously follow the Gentoo newsletters (and happen to remember all the breaking updates that have happened since the last time I updated). I'm a busy guy with lots of other concerns. It's far too easy for me to miss that Apache changed its configuration layout a couple weeks ago and find that a minor update sends me scrambling for the forums while my customer's sites are down (this happened a few months ago).

Anyway, I still like Gentoo and the ideas behind it, but it doesn't get installed on new servers anymore.