> "Actually, the problem is that out of the initial install it does so much less of what your average user wants it to do."
What version of Windows comes with an office suite, professional level photo editor, movie editor, DVD player, pdf viewer, rapid access to drivers for most printers, a software update system that handles all of their software, and a media player that plays more than just the formats endorsed for corporate control? What version of Windows has ever shipped with a game like Doom?
> 1. Learn how to interact with a new OS
This took all of setting my wife down at the computer and showing her the start menu. All the software is categorized and labeled for what it does. From day one, there was less frustration and asking for help.
> 2. Learn how to interact with all the new programs they will have to use to "replace" the ones from their old Windows environment
The high profile Linux apps tend have better laid out user interfaces, lowering the learning curve. It can be much more brutal to suffer Windows upgrades (e.g. Office 2007).
> 3. Learn how to navigate an entirely new file structure.
Are you actually more confused by having a single icon labeled "7.4 GiB Removable Media" to open the 8GB memory card in your card reader than you are by having to pick from F:, G:, H:, I:, J: and K: without any indication of which one has the card? I don't know what you're using to access your drives, but it has been quite a while since I haven't been able to just naturally access all my disks and partitions under Linux. I would never call the Windows drive letters sane, and I gave up on trying to find how to navigate my way to a different drive on Vista.
> 4. Accept that a lot of old, favorite programs just don't exist and don't have substitutes on Linux.
I'm still waiting for one to be named, and remember, if it runs on Android, it probably runs fine on the Linux desktop (with maybe a little setup). I'll throw out something on Linux that Windows doesn't have a substitute for, a prebuilt Live CD/DVD. Something valuable to me (and sometimes by extension, average users) is a good scripting language, which Linux beats Windows severely at. People find it wonderful, when you can easily piece together something automatic for them to address some preference or inconvenience.
Also, all (or at least most of) the high-end Hollywood software runs on Linux because it was easier to port to than Windows when leaving the high-end Unix workstations. With 95% of the major studio's servers and workstations running Linux, there's probably quite a bit of stuff that doesn't run on Windows, even if not all of it is marketed and sold. I would imagine some of the high-end engineering software falls into the same category, but I haven't checked.
> 5. Find out what of their hardware is "supported but not really" under Linux.
How long ago was this? Ubuntu (which is the basis of Mythbuntu) used to be really bad about access to drivers, especially proprietary ones, but they've gotten a lot better. I've had much worse problems under Windows, having to go online to fetch everything (which can be the end of the road for network drivers). It has been a long time since I've had hardware in Linux that wasn't supported from install or added automatically with a few guided clicks. Personally, I've had more problems with unsupported hardware on Windows (e.g. won't let me upgrade from the current Windows to a faster running release or driver package too big for remaining disk space).
Ooh! I just thought of software Linux doesn't have...separate update programs from every company along with some constantly running service to help launch their software faster. I suppose you could also count Internet Explorer, as it will browse the sites on the Internet that are not web sites but only Microsoft Internet Explorer sites (if there are any left). I also ran into a VPN appliance that didn't have a Linux client, but they had 100's of pages of people complaining about their terrible customer support. Their Windows client doesn't run in a Virtual Machine either.
Software previously mentioned:
> Photoshop
I remember Gimp being better than Photoshop CS1 for photo editing (features, UI layout, ease of use). They have since fallen behind, but are working on a major upgrade.
> Acrobat
There are plenty of reader programs on any platform. I'm usually in the command line, so I can just run most of the pro features from there. Does Acrobat Pro even support scripting? Linux has some ways of editing PDF's with a GUI as well, but I've never tested them. The only thing I think is missing is form support (open the document and type in the blanks), but that would be better handled with a web page, not a PDF.
> Sharepoint
I googled the program, and I'm still not sure what it specifically does other than provide Microsoft's proprietary vendor lock-in. I can collaborate remotely just fine using my phone, Skype, Google+, Google Docs and a Git service tied to project management software. The Google presentation software needs some work though. If I needed a more thorough document system that cross references other documents, I would just set up the project management's wiki.
> Call of Duty
America's Army? I don't much play FPS games, but I know there are some for Linux, including nearly all ID games.
> Quicken
GnuCash, but the market for such software is small enough that Microsoft dropped out. Most people that I know just track finances on their bank's website.
> Turbotax
All versions are available online, not just the 1040EZ (which I once did by phone).
> Support for their lousy $50 printer/copier
IIRC, all HP products are supported. I think all Epson products are supported. I'm not as sure here, but I think I remember Lexmark having full support (being formerly owned by IBM, who has a 100% Linux commitment), as well as brother. I know Canon doesn't support everything, since I have a model that Canon didn't release drivers for. It'd say it is the only product I've ever touched without Linux support, but for $40 TurboPrint supports it pretty nearly everything and gives professional level control over cheap printers. Again, this is a shrinking market.