The Black & White Nature of Gaming

The title that I'm giving this post may be a little confusing, but I hope over the next few paragraphs to bring up a point and maybe drum up a little discussion about it. This is something that I've noticed kind of recently, or at least, recently in regards to the people that I have played with the most over time. I'm not sure what other factors have gone into this, but I'll try to come up with as many variables as possible.
First of all, let me explain what I mean when I refer to the black and white nature of gaming. Do any of you that started gaming years ago, those of us that started without a number in PlayStation, or the 16-bit era, or earlier remember how difficult and challenging games were? Sure, there were limitations that ended up enforcing rules upon us that may have made the game more difficult, but they were still playable. Nowadays people talk about 'real' versus 'artificial' difficulty variances, but that's not what I mean either. 
Back in the day, games were difficult, but you wanted to finish them, so you kept trying until you won. There's a running joke that gamers are really stubborn, and instead of switching up their strategy, they'll just employ the same strategy 100+ times until they finally succeed. While I write this entry I realize that even that mentality is largely removed from gamers nowadays. There's no will to persevere, so that strategy has been for the most part abandoned among the gamers of today. What I mean by the black and white nature is that there is only winning or losing, there is no in-between. 
In our group, we have a running joke that if we lose something twice, GrimJak will get up and leave, and while we joke about it, it's actually 100% true. He doesn't want to try harder, he doesn't seek that gratification that we all used to. Instead, he either wins or loses, there is no concept of challenge for him anymore. It is true that he is the only one of us that has a more than full-time job and so he has less time to spend on gaming, but it's not just him that feels that way. Tethrinblaze for example, has tons of free time, and he also gets angry the moment he doesn't win and then doesn't want to play anymore, and comes up with some excuse why he should be mad and why he can't win, instead of trying to figure out why.
I'm the type of gamer that loves that challenge, I love overcoming some insurmountable obstacle, sometimes through sheer force of will. I'm not really a fan of that whole "Oh, I just got really lucky!" sort of gaming. If I win too much, same as lose too much, I will change what I'm doing, I get bored. Winning or losing too much is boring to me. I look for that middle ground where it could go either way, but many of my friends do not. People say a day where you don't learn anything is a day wasted, and I think that phrase applies to gaming as well. When I'm not steamrolling or being steamrolled, I love it! I actually sometimes love being steamrolled in a game, oddly enough, because it means I still have something to learn. 
What exactly happened to that expectation of a challenge? I hear of games nowadays being 'too hard' or 'too easy.' Games like Dark Souls, that are functionally the same as old school games are now referred to as "Hard" instead of challenging. Ninja Gaiden is another example, but I feel that Ninja Gaiden isn't really hard (forgive me for my blasphemous words), it's just poorly made. The number 1 killer in the Ninja Gaiden games is the camera, it's absolutely atrocious. You can't say a game is hard because the developers didn't know how to, or worse yet, chose not to implement a proper camera system. 
What I'd really like to do here is drum up a discussion about this. I know that not everyone games the same, or even has the same view, but I know that for me personally, I get a smirk on my face and a glint in my eye whenever I see something as genuinely challenging. 

My overall stance when it comes to video games