"I know others (usually younger) who'll have a Google, find a solution and implement it, but don't really understand the hows and whys, etc, and so are surprised when the same issue keeps cropping-up or the solution affects causes other issues."
This is only half of the problem. Playing with 8-bit computers was "easy" in that a single person could learn all about the hardware, the software, the ROM etc., and everything you did you were doing for the first time. Others may have already done it, but you didn't know that. Stick even a RaspPi in front of a kid today and it's likely got a full desktop OS already installed and running and it's so big and complex that it took teams of people to develop the hardware and software. And pretty much anything you can tink of to do with it has not only already been done but you can download the s/w or schematics or even buy a kit to do it. The sense of discovery is no longer there other than in the sense you are "discovering" what everyone else already knows as in all the other sciences taught in school. There's far less reward or incentive in the self-discovery we had in the 8-bit days so it needs the right teacher to inspire and right kids who want to be inspired.