Nathaniel. Very nicely put. At my last company, they bought a software solution that needed a Linux server on the backend.
Since my experience with Linux was minimal, I decided to purchase a Dell server with Red Hat Linux. (I figured that way I could get support from both companies as needed). When all was said and done, it worked the way it was supposed to. HOWEVER, to get it setup required about 3 installs of RHEL 6 (Can't remember why).
Once the OS was installed I then had to skim through both Dell and Red Hat manuals to get it to look reasonable. (Choosing and properly installing drivers for the video card and monitor. Deciding on X-Window or the other GUI. Manually adding other server component drivers. Etc etc.)
So the way I figure it, you're paying a little bit to Red Hat to make your life easier and it was still way too much work/effort.
I decided from then on I'd rather pay a little more on top of that and not have to use a command line to install drivers; or sift through obscure websites to find the sytax to install the video card because for some reason it couldn't be found by Linux.
And sure, it's nice to say it's open software and that makes it a beautiful thing; but that's a big part of the problem. People write open source and update things as hobbies, not as their main job. This makes the landscape of titles very bumpy and support for open software can not be counted on. (
Unless of course, you pay for it. But if you do, why didn't you just pay at the beginning and go with a proprietary software company with a vast number of employees?)