And generalizations about what "people" need make the mistake of assuming that all people are the same which they're obviously not.
You say tinker, I read "everything broken for non-expert users that can't compile their own kernel modules".
Tinkering is fun when all the subsystems are working flawlessly and you're just fiddling with a couple variables.
Example: "to get a complex project to compile on Windows requires a lot of tinkering".
Then thanks to the freedom to tinker I was able to get into open source software communities which gave me a career, new friends, and immeasurable amounts of learning.
That's why software freedom isn't a matter of abstract ideology to me.
Unfortunately the Linux community largely seem to attract and retain people who mainly care about their own freedom to tinker. Every time someone pushes out something broken, users lose thousands of tinkering man hours on trying to make those things work for themselves. As someone who likes to tinker, time is my most valuable commodity and Linux doesn't respect my time.
Your example is spot on. I once spent over an hour with a friend who wanted to test a multimedia application [1] on OS X and tried to help her installing it. In the end it turned out that installing the needed C compiler and SDL dependencies – a task that is only an “apt-get install” away on Debian – was a lot harder on OS X than we both had expected.
[1] IBNIZ: http://pelulamu.net/ibniz/
That you have problem running a cross platform application on a platform that has much larger ecosystem of users and experienced developers and that also have well established native alternatives is damaging the Linux ecosystem more than anything.