Just a few words on the concluding part of the Prince of Persia video. I certainly cannot imagine how I'd react to the game if I only played it for the first time nowadays, but I played it a lot back in the 90s when I was around nine or ten, and I definitely did not feel frustrated, even though I did't even realise I could save the game. I'd play it and continue when I failed until the timer ran out (I don't think I'd try going for it more than once a day), getting a little better each time. I was certainly motivated to play on and on, and not only because I had very little in terms of other games, but the game world itself was quite appealing to me, I could be lost for hours -- although as I said above, once I'd run out of time I'd usually switch to something else, like another of the few games that I had. Granted, back then I had a lot more free time and a lot fewer priorities and things to worry about in general. But it never felt hardcore or frustrating.
I dropped PoP sometime after, especially when I got introduced to Warcraft II and then StarCraft which became my next obsession. However, once I became familiar with DOSBox in the mid-2000s, I revisited Prince and, armed with my superior knowledge of the save game ability (which I gained from some game FAQ site or other, or perhaps from the Dirty Little Helper which I got from a magazine coverdisk), I was able to beat the game in a reasonable amount of time, much to my own pleasure (something like 15-20 minutes left on timer, but I might be misremembering -- perhaps it was less, but certainly not rushing in the last minute). I have to admit, it takes some practice to play, but the game controls are just perfect and fluid, once you get the proper hang of them they work like second nature. True, it's likely not something one can master in a short timespan, but I remember only pure fun playing the game, although I think I'm still scared of the choppers a tiny bit, and feared them a lot back when I was a kid 😀
I have to admit though, these days I, being interested in some obscure oldies from the DOS era or before, often run into something with hard and non-intuitive controls or game design, and it mostly causes frustration and "how could someone think it'd be fun to play THIS?!?" moments. Like recently I tried the DOS conversions of Manic Miner and Jet Set Willy (I gather that the game mechanics are in both cases accurately recreated from the ZX Spectrum originals), and, well, besides historical curiosity I'm not motivated at all to master these games, or to play them to completion, or to play them to any extent really. They are, admittedly, on a different level from Prince, being from a different time and different game culture so to speak, but I can't but think that, should I've been born a decade or so earlier and had access to a ZX Spectrum, I'd quite possibly also perceive these games in quite a different light -- because they very clearly can be mastered and played to be fun too.
I suspect that some part of the blame lies not only with me now being older and having less free time as an adult, but also in part in how the way we spend our free time has changed over these years, not in the least because of the Internet. I can easily go back in time to the 90s mentally, and the sheer enjoyment of being lost in a fun game is very obvious -- when you do not have all the distractions like YouTube and forums and whatnot. Also, many of the newer games don't put the player immediately through the gauntlet but give some time to learn the mechanics, so it's becoming less of a habit to get very invested in what could be just a casual pastime.
Of course, back in the 1990s there were also games, including platform games, that start by giving the player some easy time, but here, I think that PoP's design was not particularly conducive to this. After all, it was not called a cinematic platformer for nothing, you start with a daring escape from the prison cell and work your way through progressively more dangerous perils. BTW, have you noticed how each of the twelve levels has a unique feature that makes it different from the rest? Like a different type of mini-boss or a unique combination of traps or some story element. This is not something you often find in platform games of the era, with levels usually being more of the same with just new enemy types and/or weapons added, and a possible cosmetic change of scenery.
By the way, I do like your idea with alternate endings. Perhaps this is even something that Jordan Mechner would gladly subscribe to, but you probably know that the original Apple II game was developed under extremely strict hardware limitations that very likely prevented some of the more interesting ideas from being implemented.