I started as a MacPorts user, and moved because it managed to break itself about quarterly over the two years or so that I used it, usually in some way weird enough that it was easier to just remove all my packages (rm the whole directory) and start over than try to fix it. HomeBrew's done that zero times for me, in about eight years.
I've extensively used Portage (gentoo), rpm (Fedora, Mandrake), and dpkg/apt (Debian and Ubuntu), and MacPorts, plus put in a smaller amount of time with several others. HomeBrew is, overall, my favorite.
[EDIT] And this in particular:
> But yeah, I think both Homebrew and MacPorts still fall behind Linux / xBSD packaging systems in terms of the number of packages they have
HomeBrew has failed to have a package the fewest times of any I've used. AFAIK only Arch and Portage even come close.
[EDIT]
Downvoted for countering someone's passive-aggressive insult ("people who don't like the software I do must be gullible morons, it can't be that they have good reasons") with my own, honest anecdote, in a respectful tone. I know, I know, don't complain about DVs, but man HN, sometimes....