I'm 36 and even I didn't exactly "grow up" with computers. I saw my first personal computer when I was 10 and I didn't use them seriously until I was in my 20s. (Home computers were worthless as far as my interests (computer graphics) went, until that point). Home video is even a new thing in my life time. As a child, I did some Super8 film-making. But by my "tweens", we were using home video. I have to say, in that era the film was still much better. It was more expensive, but more user-friendly. You could get reversal film and actually cut it physically. You didn't need much gear, just a block to keep the sprocket holes lined up when you spliced the film. I used analog video in college (I wasn't doing a film major so I never got to play with film anymore other than still photography) IMHO, video has pretty much sucked up until DV and this current generation of HDV and HD. Now it's quite amazing. I mean, seriously... we have access to image making technology that back when I was getting started I would not have dared imagine I would have. (as a consumer) But you have to know a LOT about handling it for things to go smoothly. Electronic image making is more complex than film in a lot of ways. You have all the old concerns (dynamic range, exposure, lighting, composition etc) plus all the niggling technical details of the data handling and strange limitations of digital.
I brought up computers because in this era of digital video at least half of the issues involved seem computer related, or at the very least closely enough related to "computer thinking" that familiarity with computer concepts seems to help understanding. "Post production" has always been a major element in completing a project and having it look great. Back in the Super8 days... it was simple. the lab did the development and that was about it. If you got the exposure right, and kept everything in focus, you were golden. The (positive!) film you got back looked pretty good and you were ready to start editing on your little editing block. But now, there's a million places you can go wrong. And everything is your responsibility. There is no lab helping you with the technical stuff. You are not the only one that struggles with this stuff!
Ironically, professionals have a lot of help with the technical stuff. In the professional world there is probably a specialist for every area you've found yourself hung-up on!
To answer your question about expertise, I consider myself pretty high up on the photography and video/film ladder. I identified film and animation as a potential career when I was in my early 20s. Now I work professionally in visual effects (CG animation) and photography, film, and post production are my primary interests. I make short films as a hobby and I eventually hope to do it more professionally in the future. (My VFX career is healthy enough that it's hard to just walk out on though) I spent the last 20 years at least studying photography. And more than the last 15 studying and doing film, video, post production and animation (computer graphics and compositing, not traditional animation... though I have worked on a few traditional projects as a computer graphics specialist).