I completely agree on the package manager issue. I switched to OS X about 6 years ago. Before that I mainly used Arch Linux with wmii. My switch from Arch to OS X took about 6 months in which I slowly migrated. At first, it was pretty great but when I wanted to upgrade software or install some new one it was horrible. Back then I used macports and I can't remember all the problems. It was a downgrade from pacman (and apt). I gave up coding a bit because it wasn't so much fun anymore.

Lately, I started using a linux vps as my development environment and it's so much better. It's worth switching just for a good package management system.