As an amusing anecdote, my parents live thousands of miles from me. The last time I saw them I set up a Raspberry Pi with XBMC (yeah, that long ago) and a flirc IR receiver for a remote, hooked it up with local network, and an external hard drive that has a battery-backed power source. I then `dd`'d over the image onto 5 SD cards and left it with them.
Since they're in a low power-security environment, there's a lot of unexpected on-off cycles. Anyway, the whole thing still worked for them until recently and as things started failing (as they inevitably do with this max jank thing I've made them) they just figured out how to work with it.
At first, they ran out of content, so they learned how to go get it on ThePirateBay and find the right mirror.
Then OpenSubtitles (which was integrated with XBMC) stopped working on it for some reason, so they would go manually get srt files and stick them on the USB drive (visible over Samba from the network).
Then as the local external drive started failing, they used the home desktop's samba mounted drive (that I'd set up earlier).
Hilariously, the gradual collapse of the system seems to have worked as a natural training regimen, and now they're fully equipped with knowledge. So now they've got one of our old desktops in the living room hooked up to the TV, a small bluetooth keyboard lying on the coffee table, and watch pirate video on the TV.
The whole thing is positively comical because I pay for all the services so this isn't necessary at all. But availability is not complete and I'm sure it tickles them to be able to do this stuff themselves.
Anyway, thought it was a funny story. They're in their late 60s but they're doctors and last I knew, not particularly tech-savvy, so I am both proud and highly entertained.