The case for upgrades
One thing Gentoo users have noticed over the last few years is that upgrades hurt. Replacing glibc requires updating most of the system in order to ensure a smooth upgrade. Uprading gcc requires recompiling most items (for the C++ library, among other things). Upgrading other libraries is similarly daunting (expat comes to mind). Why upgrade? Seriously here; the users who love to deal with stuff, to dapple in the bleeding edge, you can stop reading now. I know why you upgrade.
But the normal user, the user using Gentoo because he likes it and it makes a good desktop. Why do you upgrade?
You see I…I use Gentoo on the server mostly…I have a PPC based Powerbook with OSX on it and it serves as a decent desktop box, but Gentoo is on the server. The Servers…never get upgraded, except for security issues. I let all the crazy people who aren’t reading this (since I told them to stop reading above) hit all the fun cases and plan my server upgrades accordingly.
I have one Gentoo desktop. I upgrade maybe every 3 months. Upgrade cases are similar to servers, if I need a new feature, a GLSA, or a showstopper bug that requires an upgrade.
So I ask a certian class of users why upgrade? Do you even know what you are upgrading to? Is there a deficiency in your current system, features you don’t need, showstopping bugs, or security issues?
The case for upgrading for me just doesn’t come up often.

Excellent post. Very timely in fact because I was almost about to upgrade glibc on my ultra-stable mythtv box to version 2.4. Why? No real reason, it’s just been bugging me. I had masked 2.4 for a while now. It came along at the same time as gcc-4 game out and I masked both. I don’t know what made me want to upgrade to glibc-2.4 today. The change to mandatory nptlonly is bound to cause problems. I already had a problem updating glibc before on that same box. After reading your post I went and stopped the compile. I am just asking for problems, and believe me I have had problems on this mythtv box in the past, almost always due to upgrades of some package.
I have now resolved to never upgrade any major packages again, I’m going to leave it all at mysql-4*, mythtv-0.19*, gcc-3*, glibc-2.3*, kernel-2.6.15*, ivtv-0.4*
I should treat this mythtv box as a server and I should also start treating my desktop more like one.
At least a couple of reasons:
* I want to test new stuff before “real” users hit it
* I don’t have time to do research on new features for every single application on my system, but I do expect that useful ones will show up, particularly in GUI software. A lot of CLI stuff is mature enough at this point that releases are mostly bugfixes, so they’re more unlikely to introduce regressions.
I update not only to see what’s new, but to give back in my small way of being a helper QA :).
Because the more one waits, the more painful the next upgrade becomes…
Also because emerge -uavDN world && revdep-rebuild is a good way to know your system is not too messed up after your “oh let’s try all those cute little apps there ” frenzy.
And also because maintaining a sensible /etc/portage/* is boring, and quite difficult.
(Most os those point are probably at lot less valid for a server, where you are supposed to pay much more attention to what software you use).
I think it’s easier to fix the small bugs that you hit from doing frequent small upgrades than to fix the huge pileups that happen from upgrading all-at-once infrequently. Besides, if an inexperienced user upgrades infrequently he will not gain as much experience, and what he does gain, he’ll gain in a violent and unpleasant way.
Gentoo documentation is better suited to help users do regular world updates than to help users recover from long out-of-dateness
I upgrade almost daily - because it leads to LESS breakage. I know several gentoo users personally and the less someone updates (once a week, once a month, once every couple of month), the bigger the problems they hit. I have and had some. Almost always minor stuff. I hit them, I solve them (by searching for answers), and some days later, I tell some of my friends how to solve the problem, when they hit it. But once in a while, one of the seldomly-updaters makes his update and hits a problem, I never saw - because for some reason, an unstable system is more stable than a stable one…