I had much experience with ports about 10 years ago building from source and even maintaining and creating a few. I can say the community around ports and specifically Marc Espie were great.
I also always found ports and OpenBSD to be explainable, non-surprising and simple as opposed to much of what I saw with rpm and apt.
Ports work pretty well and without much hassle. In contrast, rpm and apt are pretty complex. I've never felt I've understood them. If using Linux, I very much prefer pacman.
However, all seem to be stuck in the past. I wonder why the ideas pioneered by http://www.gobolinux.org/ are not more widely implemented, leaving nix aside.
I also always found ports and OpenBSD to be explainable, non-surprising and simple as opposed to much of what I saw with rpm and apt.