Yes, I've run into a few of these points often enough to see that we really need to find a better way to bring ease of use and intuitive designs for technology aimed at people who did not grow up with it.
Having moved from the east coast to the west, I often will try to find a way to get my mom to Skype/Google+ so we can see and talk to each other. However, it usually winds up turning into a phone call and me emailing pictures to her.
I love all that technology has to offer, but at the same time I hate the perceived limitation that we've made leaps and bounds when things like the above still are an issue.
*note: I'm speaking only about the benefit of consumer tech to parents/baby boomers, and not about things such as advancements in the medical field, automobiles, etc.