The tale of Miguel de Icaza and the Mac
I just finished reading this: http://tirania.org/blog/archive/2013/Mar-05.html
I couldn't find a thread here that discussed this, but maybe there is one. I tend to think that a lot of the reason the GNU/Linux desktop hasn't "crossed the desktop chasm" is hardware. Miguel sites in his blog that he has had hardware problems that were frustrating. I think this is a big problem too. Hardware is one of the areas that we can't just write a new program real easily to fix. Graphics cards are a great example. Printers, wifi and other things are challenging too.
He also sites packages and compatibility. I see that as a problem as well but that can be addressed per distro. This illustrates that the cause really should be freedom and not convenience, though convenience should be a goal as well.
Interestingly enough, Miquel de Icaza posted a response on this blog:
http://threads2.scripting.com/2013/march/whyWindowsLostToMac
I personally think it would be great to see hardware companies spring up that are 100% in support of free software. Companies that manufacture hardware components. I know Think Penguin exists and I'm really glad they do but lack of supported modern hardware is a challenge for many users.
Printers are never a problem if you buy from right company. HP Linux driver is fully free. http://hplipopensource.com/hplip-web/index.html
Now back on topic. Problem is not that you cannot find good free driver for any graphic card out there, infact, most of the people do not care about freedom: They care about utility. Ubuntu is great example. With nonfree firmware, drivers and software like steam in Software Center Ubuntu started showing some utility (and rapidly gaining popularity).
The real reasons why GNU/Linux "hasn't crossed the desktop chasm" can really be fixed by writing programs. Here are few problems I encountered trying to promote GNU/Linux:
1) Lack of specialized software: While I was able to offer wide range of software to an artist (gimp, inkscape, scribus, blender...) I couldn't offer anything to civil engineer. Sure, there is FreeCAD but due to stubbornness of rms it doesn't load DWG files. Read:
http://libregraphicsworld.org/blog/entry/libredwg-drama-the-end-or-the-new-beginning
and:
http://libregraphicsworld.org/blog/entry/whats-up-with-dwg-adoption-in-free-software
2) Shockwave Flash. Gnash looked promising, but development is stalled. It can play youtube videos which aren't avaliable on html5, but won't stream some other sites. (Notably, it won't stream any anime)
3) Bugs. I noticed interesting phenomenon: Average end user is MUCH MORE capable of finding bugs than programmer or superuser. While I am generally not affected by bugs, those on whose computers I installed GNU/Linux on are. I feel like tech support :/
4) Fragmentation. Why is there qcad and freecad? Why is there gnash and lightspark? Why are there totem and vlc? Side effect of this is: Lightspark plays avm2, gnash doesn't. However, lightspark can't play some stuff gnash plays so you end up installing both. It gets more ridicilous: vlc streams rtmp, totem doesnt. totem streams mms, vlc doesn't.
Oh and not to mention all the effort wasted on features offered by both options.
Some projects made with Blender and FreeCAD: http://yorik.uncreated.net/
Are Blender and FreeCAD cool? Yup.
Can they import dwg? Nop.
Without complete dwg support they aren't usefull, especially to students since every school in my country uses AutoCAD.
IMHO is strange like many "free software supporters" for years (10 years or more) buy bad computers today. If you live in the US why not buy in ThinkPenguin? If I want do buy one I need to pay shipping and 60% of tax... I need to pay two laptops and receive one ;-)
Is the better company sell x86 computers compatible with 100% free software. Any distro can run (100% free or not).
Is very common you see in GNOME Planet, KDE Planet and many blogs about "the big frustration" about the new laptop with Windows 7 or Windows 8 (paying for Microsoft for after remove this for install Fedora, Ubuntu, OpenSuse, Mint...) of Dell, Lenovo, Apple, HP, Acer, Asus (with Intel Centrino, Broadcom, NVIDIA, AMD Randeon...)
Big question is why do they buy laptop with Windows regardless of vendor if they don't want Windows. I never understood that :/ Asus offers No-OS laptops. As a bonus, its cheaper!