The next model will take their design in a new bold direction, and actually function as a trash can.

Of course it'll require proprietary trash liners and will require an adapter to deal with various forms of trash.

My Grandma is happily uses Linux. All she cares about it being able to get to email.
My Parents actually asked me to switch them back to Linux because they kept having troubles with Windows 7.
My Uncle uses a Chromebook, because they are really hard to screw up and easy to repair.

Encouraging the people I know to switch to Linux has dramatically cut down the number of times I get asked to fix something. Something like Linux Mint just works and tends to be more responsive. It also doesn't have Windows' bad tendency to demand that you restart because it just installed updates.

On the flip side, there are plenty of people I would recommend Windows or OSX to. Normally it's because they need/want to use an application that just isn't available under Linux. I feel like the learning curve for casual use for someone going from Windows 7 to Windows 10 might actually be worse than going from Windows 7 to Linux Mint, Ubuntu, or OSX though.

Ubuntu gives you an option to do an in-place upgrade through their upgrade gui, and it's worked just fine for me the several times I've used it.

Under Linux Mint it's been a bit trickier, but not really that bad. I wish they handled the in-place upgrade stuff a bit better, but on the flip side the rest of the OS works really well for me and has many of the tweaks I'd normally apply to Ubuntu already done. With Mint 17 you actually can upgrade in-place to the point releases which seem to be tracking some upstream changes.

While I find the short support times annoying, I find it acceptable that a short term release becomes unsupported quickly. The LTS releases from Ubuntu get security patches for 5 years, and you don't have to pay them any money for the service.

Also whining about having to use the command line is like whining about having to drive stick instead of automatic. Automatic is pretty easy, but once you learn it, driving stick is not much more difficult and many people actually enjoy driving that way.

That particular link doesn't work for me, but the point does stand. Velcro ties are the way to go.
I've got these Velcro cable ties from Home Depot. 50 8 inch Velcro Ties Though at $5.27 each you can definitely find better deals. But being able to just walk in and buy them without waiting for shipping is worth it for small jobs.

If you want to be really fancy then I would also get some kind of way to label or at least mark your cables on both ends. It really does pay off when you have to move, or fix something. My wife went through our entertainment center and labelled all the cables with some blue painters tape and a sharpie. I'm glad for that every time I have to go back there and mess with something.