[] Do you enjoy building everything to the minutest specification, regardless of bins being available?
[] Do you like the idea of building/rebuilding the entire system into your hardware instead of performing a quick fresh installation?
[] Let's say you've been lazy with updates -- would you mind emerge ragging the CPU for 15+ hours?
(Disclosure: I love Arch but (believe it or not) I've been die-hard Gentoo for a couple of years, even got two versions of the same T-Shirt -- which I feel is appropriate)
It was no.3 that eventually killed Gentoo for me. Took a three week holiday and it must've been a busy release period or something, because when I came back I had an unholy hell of packages needing updating.
The worst part was there were multiple dependencies that just wouldn't compile. I fixed the first couple, but when you have a 3hr+ OpenOffice compile fail on you inexplicably... I just want my computer to work without worrying about all that! It used to be that people would say "Then why are you using Linux? go back to Win/Mac", but nowadays a perfectly stable, maintainable and fast Linux is easily achievable. I think this is the major reason behind Gentoo's declining popularity recently.
Having said that, I learnt a huge amount about Linux just by unbreaking all the bizarre things that risky Gentoo emerges did to my system :)
Ultimately, it all comes down to how I'd rather spend my time. Hours and hours every month running a big emerge on Gentoo, or a few seconds in pacman on Arch? I have work to do on my computer and eventually the process of just running the Gentoo updates was occupying too much time that I could be spending on actual work.
This too is why I switched to Arch for my new desktop I built last month.
Forget to update for a while? Good luck getting your system into a sane state ever again. Better yet, if you go a while without updating, you'll wind up with package conflicts in your dependency graph (the worst is the dreaded "package X and package Y both insist on different versions of the same dependency"), and it'll take you forever to manually untangle them.
I've been using Gentoo as my main since 2004 or 2005, though I had some Arch experience from my work desktop at my last job (I installed Arch on it because I wanted something Gentoo-like but wasn't about to risk Compile Hell when I had deadlines to pay attention to). The decision to switch wasn't an easy one, but it's been very rewarding. I'm still of the opinion that portage is the best package management system I've used (it's not just for compiling stuff from source: there's no reason someone can't build a binary distro using portage), but pacman is a pretty damn close second, and I'll take pacman's lack of flexibility over Compile Hell any day.
I still have conflicting thoughts about systemd. I actually ripped it out on my old work computer and replaced it with OpenRC (to fulfil my goal of "something Gentoo-like but without all the compiling"), but on this machine I decided I'd keep systemd around for at least a few weeks because I wanted to get out of my comfort zone and learn something new. Now, I'm not sure what to do. I've discovered there's a bunch of stuff to really like about systemd (in particular, "systemctl status" is amazing), but on the other hand, I really miss OpenRC, and I happen to prefer its idioms over systemd's (I'm sorry, but you will never convince me that INI-style syntax isn't the ugliest thing ever).
Soon to be 10 year gentoo user. I've toyed with various update frequencies, and have found that multiple weekly updates is a good way to stay sane. That said, there are those time where you just have to help an emerge see itself through.
I originally came to learn, but I've stayed for the USE flags. The number of times I have needed or wanted some feature on a package in arch (which I use for my linux vms) and have had to dig through the documentation and set up a compile environment for a package for an hour is absurd when I realize that all this is solved in 30 seconds by setting the right USE flag on gentoo.
Gentoo also has the best/most up to date python support of any distro I have found.
Also I've found PKGBUILDs very simple to tweak if you need something extra. If you do start using the AUR, I recommend getting yaourt and letting it take care of that for you. I rarely use pacman directly, as yaourt takes the same flags and works for the arch repos as well as the AUR, plus it allows you to search for packages by omitting -S.
Personally I'm not a huge fan of Gentoo, I used it on my desktop years ago and ended up breaking things weekly when portage got cranky. Currently I manage a few thousand gentoo servers, and find it tedious and frustrating at the best of times. Clients refuse to upgrade for too long, so upgrades generally mean a reinstall. And as customizable as it is, if you wanna do something outside portage, everything will inevitably break.
Good to hear from such a long term user! I can't really see my enjoyment for the system waning any time soon; feel pretty at home with Gentoo. I hear that a lot about staying for the USE flags, and it's becoming a similar story for me.
I'll keep that in mind about the update frequency.
My latest gentoo discovery: sys-fs/static, took me some time though to setup the system. Server runs for couple of months now without any problems. And completely free of systemd, pulseaudio, and udevd.