Well, the issue is mostly that older people don't want to learn or change, they have gotten by through most, or all, of their lifetimes with a specific set of skills, expectations, and technology, and resent basically being told that they have to change and do things differantly, in many cases to accomplish what they were doing before. There is a sort of "proud to be ignorant" culture among the older generations, with new technology being an obstacle, as a result they attempt to get through it while proudly acheiving no understanding.
There is a flip side to "the technological incompetance of my parents" stories, which is where you have older folks making jokes about the stupidity of whatever the current tech is, being needlessly complicated to do the same things.
To some extent there are valid points on both sides. The new technology is arguably better and can do more, and it's dumb to hold back progression due to older folks not wanting to adapt. At the same time though basic functionality gets lost behind layers of additional features. Even as someone who understands it, I do not for example see why you need multiple layers of menus to just watch and control a TV. Someone who is older and grew up and lived just having to flip "on" and then use a channel selector has a valid point about a lot of digital systems. Not to mention the way they intergrate pay and premium channels into a lot of base menus to try and convince you to buy them, which is annoying, you don't have to be older to be bugged by obtrusive advertising.
Of course then again one of the problems with this is that you have lawmakers and politicians who are generally older passing laws about technology they don't understand (and really don't want to) and with most of the money in the hands of older folks, in many cases working to oppose new technology simply to maintain the status quo for whatever generation they happen to be from.
It's messed up all around, to be honest on a lot of levels I think the problem is that the guys developing technology don't understand what "user friendly" actually means. They also put too much attention on extra features rather than basic functionality when operating a device. When say making a basic phone call is treated like just another function along with all the other things your "smartphone" can do, that's a problem, since that's the primary function of the device. When the basic functionality needs special lock settings to prevent it from interfering with other functions and such I think that's also an issue (and think about that somttime, a lot of times your cellphone doesn't lockout the phone functons to prevent it from dialing while folded up or whatever).
Apologies for all the rambling thoughts.
--and then he buys the complete pack from the company's website ($40) a week later, haha. He doesn't understand DLC; you didn't have to re-buy the whole game to get the extra stuff, Dad), Sim City, Sim Tower, Rollercoaster Tycoon and Call of Duty (the first one, on PC). I'm trying to convince him to try Portal; not sure why but I really want him to play it. 
