In general, Debian tends to ship with outdated and broken software that is not recommended by the upstream devs. And Debian support, which you of course have to use, since no upstream devs will bother with you as long as you run ancient versions that Debian have patched beyond FUBAR anyways, is a tiresome slow mess to deal with. So you end up building from source, and the build systems on Debian (yes, there are several) are far from elegant and easy to use.
I ended up moving from Red Hat to Gentoo years ago because I got sick of RPMs and
source builds creating a mess in a system. Red Hat was good so long as you only used their packages. The number of times I sat their scratching my head when RH was asking for x.y.so.n and no RPM could be found to supply it :-)
Gentoo was great because you could have a bleeding edge install (and all of the associated "features") or something a little more stable - and portage did a fairly good job of keeping everything in order. The downside I found was that if you left a significant period between world syncs (ie, > 3mths) you'd find that they'd moved so far forward it was easier just to do a full reinstall.
Now I'm back to Ubuntu because I really don't want to waste time building everything from source - whats the point of portage if you're going to be using PORTAGE_BINHOST for everything? ;-) And Ubuntu packaging seems to be fairly well done .. well, better then RH ever was.
Of course, if Unity/Gnome3 continue to be pains and Ubuntu insists on pushing Unity onto us, then I might reconsider Gentoo.
For the record, I use Debian and Ubuntu professionally, I get paid for installing and maintaining Debian and Ubuntu systems, I get paid for packing software for Debian and Ubuntu systems. Do I enjoy it? Not much, it's quite often a PITA and reporting bugs is tiresome, they take forever (months and years) to get fixed. Privatly I run Gentoo on around 20-30 machines of a wide range of systems and architectures.
lol, I had the opposite - paid to install and maintain Gentoo systems (probably close to a hundred over a couple of years) yet at the same time having a growing number of Ubuntu machines running loose within the family.