Hi there @papayas! First of all, welcome to Steemit :-)
I loved reading through this post. Hearing about your frustrations in early games and how they taught you so much. I think you're right about the 'new age of gaming', people expect to finish the game. If they are stuck, they will google the answer. I will admit I do the same thing, because I love exploring the most and I want to be able to see everything!
I remember back when my brother had the N64 with Zelda, Ocarina of Time. I loved, loved, loved that game! But at certain points, I got stuck. I tried to continue on my own, but after an hour or so, I just had to ask my brother for help. I just wanted to see more! I never did finish that game, as I got stuck in the underwater world and eventually gave up. Still one of the best games I've played :-)
Anyway, I think it's a great idea to have your kid play the harder games first and learn to figure stuff out on his own. I hope he'll just carve for more and won't give up!
I totally see your point. Ocarina is one of my favorite games of all time and I still go back once every few years and run a play through. I like to run those games to completion without google for the added challenge, but yea, there are times when I am sick and tired of the Water Temple or looking for those golden skultulas that I break down and google it. I have to give Zelda credit for coming up with some of the most challenging dungeons I've played. BOTW wasn't as challenging, but they changed that game up so much that it felt like a different kind of challenge that was fresh and really enjoyable. Still not sure how I feel about them jumping on the DLC/season pass boat though. Have to wait until the second one drops soon!