I just added you to my Google+ circle Ben. If people do not take creative criticism when they are wanting to do this kind of stuff. Then we just end up with the same old stuff.
I would say the biggest thing that we see is the fear of trying something new, when it comes to people asking how to do stuff with Windows 8. Most are so used to Windows 7 or Vista. That they get the Metro interface and feel so overwhelmed. Then add to that all of the writer noise from various publications that do not even show people simple things.
I always point people to the likes of slipstick.com or ezlan.net for stuff. Even when you try to explain how to do stuff in the Command Window. A lot feel that they are now getting that Deer in the Headlights look.
I taught myself a lot of this stuff. What I did not learn on my own, I reaped from the posts in forums like this when I would hit a brick wall.
Even putting together a video on how to connect stuff like a Chromecast or Amazon Fire Streaming box would be great. I tried to even find simple tutorials for my 74 year old mother, to teach her how to use her Samsung Galaxy Tab 3. I cannot find anything that simply explains how to turn back on Wifi, use email, the touch interface, etc..
I basically gave it to her and said "Her mom. This is how you bring up the icons. This is how you get to Facebook. This is how you bring up the Walgreen's app, etc.." I usually have to run down to her place five minutes away, to turn back on her wifi. Because she still cannot get the whole swipe or how to fix something. All because the simple stuff like that is not covered in videos. Or they are too plain and not detailed in steps as they should be.
Everything is becoming like Common Core in school these days.