Gotta say, fellas, Gentoo is very comfy after you get past the learning curve. Really makes you appreciate the work that goes into binary distros. Also learning more and more about compiler optimisations and LTO has been quite fun.
I'm sure eventually I'll hit a package that fails to install or an update that fails and ragequit, but the honeymoon period of a couple months has been quite nice.
My advice to avoid problems. Update regularly.
In my time using it. And I have seen others that use Gentoo generally do the same. Update when you got to sleep, or if you are away from the computer you use it on during the day for work or something, update then. That way, even large programs getting updated really doesn't matter.
The reason I say to update regularly, is because when you don't. You are a lot more likely to run into wierd dependency conflicts. Or use flag conflicts, that can be pretty difficult to solve. Or at least take time to figure out. If not unemerging something, doing the update then re-emerging. When you stay up to date, if not everyday, at least every other day. You pretty much never have any of those issues.
Also if you don't update for a week or multiple. Then you actually start to potentially run into giant updates that will actually take a while. So just getting into the habit of getting it done at the end of the night or whenever. Makes life pretty easy. Really it's no more tedious than running arch, or any other distro when done like that.
The build failure thing. Can be frustrating when you run into it. I just tend to run a fairly minimal set of packages, nothing too crazy. I find that helps a lot. I ended up seeing where I could cut fat in my system, forced myself to learn to do more of what I normally do manually. So I don't have to keep a bunch of packages I don't actually need.
Overall I've liked learning a lot of it, and it's pretty useful. Like learning a bit of shell scripting. That kind of thing. Can actually do a lot of the stuff you might install a package to handle. Also just kinda fun to challenge myself to see if I can do the stuff on my own. But that's just me being a Linux sperg.