I used FreeBSD for a while because it had ZFS, and found Ports confusing and fragile. Maybe I was doing it wrong, but the handbook wasn't much use: "here's 4 different ways to do it, we're not saying which is a good idea". Every upgrade took ages, required reading a load of documents, and broke something.
There didn't seem to be an equivalent of Debian's Stable, everything was apparently the latest release.
I have OpenBSD, FreeBSD, and Red Hat 6 (government wanted some software run and guess who gets the $) running in my server room.
Red Hat seems to be fine with yum, and I haven't had a problem yet. FreeBSD's pkg (pkg-ng technically) is ok, but I keep running into problems on upgrading because someone split a pkg or renamed it. I search but don't find a simple solution. I haven't had any problem on the OpenBSD side, but that could be because every 6 months do an upgrade with the new release. Patches are a bit harder on OpenBSD unless freebsd-update does something weird. the whole src thing in the freebsd-update bit me.
I also was frustrated with how poorly the handbook explained ports/packages. But now that I understand how they work, I feel like it’s an elegant system that works well. I just wish it didn’t take so much trial and error to figure it out.
That's what the mailing list and the forum is for where you'd most likely told to just use 'portmaster' which is the easiest. Not that the others aren't easy, too, but it keeps tabs on dependencies for you but its best to pick one method and stick to it.
There didn't seem to be an equivalent of Debian's Stable, everything was apparently the latest release.