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So far, I've been using Gentoo linux for a very long time. And it still is my fav distro.

On a few computers, I've been using (K)Ubuntu for practical reasons. It is undeniable that Gentoo does not perfom very well on old HW: you have to compile everything from the scratch, it can take a day on a pentium III.
Also, Gentoo requires that you actually know of what you're doing, both when you install the system and when you perform a update. No worries, everything is very well documented. And you learn a lot on how-it-works behind your WM.

Still, I do prefer the Gentoo way: you only install what you need. Nothing more. No waste of space for that-program-you'll-never-use. And when you don't have it installed, you don't have to worry about security ...
Your system is automagically consistent. Always. You can still break a Gentoo system, but you really need to put some effort into it.
IMHO, Gentoo is a matter of control.

Back to the topic.. we are talking about upgrades, right?

What I usually do on my Gentoo machines, is to run

# emerge --sync
# emerge -puDv world

once in a week or such. When I'm sure of what emerge is going to do, I run it again without the 'p'.
And after each update I run

# etc-update
# revdep-rebuild

.. just in case ;)

No troubles at all. I run it on a Compaq EVO n 400 and it works good for me. It can take some time to recompile KDE, but, hey, you can just stop the emerge and re-schedule it.

On the other hand, (K)Ubuntu is (usually...) a click-click-update game. It can be quite handy when you do not own the computer. And if you know what you're doing, you can always play the apt-get game instead.
I actually enjoy this on my local Red Cross group computer. And on my mother's laptop. SSH rocks.
(yes, my mother uses Linux. cool, isn't it?)

But today, the (K)Ubuntu upgrade surprised me.
I was going to locally upgrade a 7.04 Feisty Fawn. I followed a official how-to, and as first thing I upgraded to 7.10 Gutsy Gibbon using Adept.
It automagically screwed up X and a few other things. Nothing too bad for me, I mean... I use a Gentoo, I remember each single conf file and can blind type a new one in a minute.
"X fixed, let's continue the jo..." ... system freezes under my eyes. Twice. No reason. Control-Alt-F1 did nothing. And it was neither the RAM nor the HDD,  I'm writing this post on the same computer.
I had to restart pushing a button, and go a few times through

# dpkg --configure -a

(I hate to type sudo followed by command... I switch to root with sudo su, instead :p)

at last, I got a working 7.10 system.

I performed the next step in a terminal. At least, it showed up what it was doing exactly :p

# do-release-upgrade

(I told you I hate sudo, right?)

did the trick. Almost painlessly ...
I had to manually fix a couple of things, but it worked quite good compared to the 7.04 -> 7-10 upgrade.

At the end of the story, I'm still of my opinion: (K)Ubuntu gives you a faster (easier) way to keep a system up-to-date. But I still enjoy Gentoo on my own computers.

End of the rant ;)