That's an interesting analogy, but I don't really think it holds water: older editions of D&D are far more accessible than old console games. the 'advancement" of presentation and techniques is very real (hello, Advantage/Disadvantage!), but I can say as someone who tried AD&D after 4E came out in my 20's, it's not as obsolete the same way that tech dependent entertainment is.As much as it pains me to say it, nothing in D&D prior to 2014 has much significance on most current players.
If we look at it like console generations for video games, these are my analogies.
D&D 5e = PS4/Xbox One era (been out forever, feeling clunky and long-in-the-tooth, but no one has really had a good reason or ability to upgrade)
D&D 4e = Sega Dreamcast (the system fans love it, most people have never played it, and it crashed quickly)
3.x = PS2 (the basis of modern game design, but clunky, slow, and you probably don't want to go back to it. also your first DVD player/d20 game)
AD&D = NES (primitive, good for old timer nostalgia. you recognize some of the characters from this era, but if you're a modern player you don't want to play these games)
OD&D/Basic = Pong console (it can do one game, the controls are weird, graphic are primitive. some people can still play for hours and enjoy it, but has little appeal to modern audiences. still, if you look closely enough, you can see the origins.)
Dreamcast or Wii U are a pretty apt comparison for the market position of 4E, though, to be honest. ouch.