Sounds like OP has a plan, but I had to chime in with some sympathy for dealing with the technophobic.
I learned computers when they first came into grade school - no mouse, floppy disks were really floppy, DOS (the only windows where the glass ones in the wall), and the only thing I remember doing besides practicing keyboard skills ("a-s-d-f [spacebar] j-k-l-; [spacebar]"

), was playing Oregon Trail (shooting square bullets at white 2-D squirrels and buffalo was fun...as was naming members of my party after people I didn't like, then choosing to do things like soldier on instead of rest when they got snakebit or dysentery.

)
I've gone from having a PC with Windows 98 to the Windows 7 laptop I'm typing this on now.
I built my own tower PC over 7 years ago. A lot of research. A lot of work. I don't have the patience anymore. I would classify myself as Intermediate when it comes to computer skills. I haven't been keeping up with hardware or programs.
My father...still uses a
typewriter. At least it's an electric one, but still...*SIGH*
I remember I tried to teach him how to use Word...I told him he just had to type - he didn't understand word "wrap," so he kept hitting "Enter" when he got to the end of the screen and it was all capital letters down the left side. He said it was "too complicated." Oy...
No one knows everything. My brother is an engineer who self-taught himself computers and then a few years ago went back to school and took a course in computer forensics. He is a genius with computers compared to most...and yet
I had to teach him how to use Ctrl + Shift to select multiple files! He had been doing it one file at a time (Ctrl + L Click) before then!

My brother once pointed out that computer programs often have a steep learning curve because they are made by programmers who forget they are not talking to other programmers. Most programs are not very intuitive, and if you have not grown up with computers you are at a distinct disadvantage. You are basically trying to learn a foreign language combined with a physical routine you have never before performed. I agree with PPs that few are unteachable unless they do not want to learn, but it is important to consider to magnitude of what you are asking them to comprehend.
Lastly, I would like to add my dismay that there are people in healthcare that cannot or will not adapt to technology. My healthcare provider has created a very strong online community. I can log into my account to make and see upcoming appointments, order medication, see test results, or ask my doctor questions that don't require an appointment. A healthcare professional who was not computer literate would find it very difficult to function in my provider's network!
Learning a completely new thing is very stressful and intimidating...but gaining even the most basic competency not only does wonders for one's self-esteem, but opens new doors and allows you to explore what you are passionate about in new ways.