I had to babysit OS X a lot more than I had to babysit Linux. Ubuntu might take one or two tweaks when installing on a MacBook, but twenty minutes later it runs perfectly for ever (or six month, whichever comes first).
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.
> 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.
I somewhat disagree with homebrew being thrown in with Fink and Macports. The benefit to homebrew is that it doesn't require having package maintainers to babysit packages and make sure the binaries work and are updated. You basically just take the raw source and someone throws a patch on it. It's actually a thousand times better because you don't have to worry about compiling binaries that work on everyone else's systems no matter what crazy config they have.
What I was trying to get at is that those systems were unsustainable and I can see homebrew developing into a legitimate "default" package manager that is infinitely maintainable rather than Fink/Macports which were simply shims that were doomed to fail by their architecture.
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.