With games, I think it's a bit real culture change and a bit of generation kvetching, honestly. There are some objective factors, like games didn't used to have tutorials because memory was too precious to use on them. As such, there was no ramp up, you have to have a base level of skill of familiarity that even reading the manual might not prep you for, and that initial skill wall could cloud your vision of the whole game, even if it isn't actually hard past the learning phase.
Also, if ytou are going real old-school, a lot of those games were arcade ports, and arcade games WERE harder for one very specific reason, and that was to extract quarters from your pocket.
As for shows, well, there were plenty of shows back when that were episodic in nature, which means that every episode kinda reset the stage. Ongoing storylines were just for soap operas for a long time. Twin Peaks is often credited as the show that made season-long arcs a mainstream thing, and that wore it's soap opera influence on it's sleeve. Other shows at the time like Star Trek or The Wonder Years rarely kept consistent plot elements from episode to episode. It did happen, but not in the way that some of the shows nowadays do it, where a season is essentially an 8 hour movie. As such, you could jump in pretty much anywhere and miss a few episodes. This was also done for the practical reason of broadcast tv, if you didn't see it on time, you would have to wait for a rerun or just be out of luck, so most shows kept it simple with the episodic reset. Better that than lose viewership because they had to work through the broadcast time.
Your dialogue example absolutely happened back in the day, too. The "As you know..." lines and backstory fill-ins were just as ham-fisted then as it ever got to be. As a certified old fuck, I remember because I was there and also I re-watch old shows quite often.
One thing that is worse, though, is the snarkification of characters. Like everyone is a "confident, quirky" character, and that has flattened out personalities in shows in a way that can make some more modern shows bland and seem "easier." Like many things in life, I blame Joss Whedon.
But on the whole, I think shows are just as smart and hard as anything in the past, and also just as stupid and easy. It is possible there are more easy shows now just because there are a lot more shows period. Like, I feel anything with The CW logo on it is easy, simple and shockingly numerous.
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