I had to babysit OS X all the time, due to its lack of a good package manager. This was years ago, I don't know if it has improved, but it grated me greatly.
Well of course, OS X has heavily improved since the early days (I'd call 'early' everything below 10.4). The surge of developers wanting to use OS X has also increased the demand for package managers, and so they came. First fink, then macports and nowadays most use homebrew. You install them once using the standard OS X pkg installation facility and then you're good to go - the range of 'backend software' packages in brew is comparable to apt-get I'd say. For everything from linux that needs a GUI I have a VM, for everything Windows-only I have another VM. There's never even a question whether I can run something locally - once you have that it's hard to give it up again really.
That being said, the best OS X release is probably 10.6, since then I don't like the direction very much - but on macs you're basically forced to use the newest OS (XCode compatibility, hardware compatibility once you upgrade your macbook). The iOSification hasn't been a dealbreaker to me so far, it's IMO still a better all round experience than any other notebook, especially considering the service quality, which is bar none where I live. Friend of mine bought a $2.5k lenovo - the board went dead after 1 month, they picked it up and he hasn't seen it since the last six weeks, no replacement. I had a similar issue with my rMBP - got it back, fixed, after 2 days. Similar stories about Dell. HP might be better, but their hardware is crap IMO. I just can't trust any other laptop manufacturer at the moment, which makes me sad.
Fink was only out of date because they weren't keeping it up-to-date (perhaps their builds weren't automated? That's pure speculation, I have no idea). Debian manages to keep things more or less up-to-date with more packages (and architectures) than Fink ever had.
Incidentally, if you put your Homebrew in /usr/local then it will often install using the "pour" technique which is pure binary distribution.
I loved Fink until it started languishing, and I love homebrew now: its "everything in git" philosophy and very-open-to-pull-request attitude of the maintainer make me optimistic that it won't slow down and become irrelevant like Fink did. I think that's the real difference between the projects.