I really like pkgsrc. It’s a big system that works well for managing a huge variety of software packages, across multiple platforms, and it’s been beneficial to DragonFly for making a lot of programs instantly accessible.
The issue nobody’s fixed – yet – is that there are plenty of ways to upgrade, some of which don’t work (make update), or involved homegrown solutions that miss the goal most people have: the ability to say simply “Upgrade this” and have it work. This is why programs with the same functionality but simpler usage become popular.
(Prompted by a number of recent “How do I upgrade pkgsrc?” questions on DragonFly and pkgsrc mailing lists.)