I think that segment falls under the 'diffcult until the layout is memorized' type.  Memorable and difficult in it's on right for sure.

Timesplitters 2 Atom Smasher on hard difficulty. Wow. Trying to delay the bombs in that time frame while taking out baddies was straight up brutal. Yet...the level was enjoyable and dared you to keep trying.  Each 'wave' was well paced(much lie the rest of the game) and challenging. Love it.

Dragon Age Origins final boss battle and Demon's Souls Maneater. Maneater was more difficult(i.e cheap difficult) but DA Origins final boss battle was better, and required a lot of strategy. Almost my favorite boss battle hadn't it been one another boss battle in Demon's Souls.

A lot of boss battles in D Souls is brilliant.

The first image in your OP is unimportant because games nowadays can span upto a long time like 30 plus hours and checkpoints and save points are necessary. In olden days the only genre was the 2D platforming kind so it didn't matter that much, but now it does. It was also a problem related to tech and not just to increase the difficulty. But that's just being off topic so I will stop.

I understand the whole "Hard because it requires memorization" factor.  And I agree that it exists.  But if you are slightly skilled you can surpass some hard sections by thinking on the spot even with encountering it for the first time, and that is very rewarding in a creative type of way.

But overall there is no way one can surpass such a segment like that without trial and error at least quite a bit.  And that is mainly because of the sections where the passage way is shaped at the EXACT measurements of the character.

When a few of my friends got better then me in Starcraft:Brood War.

Resulted in some absolutely epic games, that I eventually lost...

All of Donkey Kong Country Returns secret temple levels.

I am not unfairly bumping them, but just learning how to take the inside line and knowing how far I can push it before it disqualifies me. I am not just playing bumper cars

Oh man, Ruby weapon from FF7 and Omega weapon from FF8 come quickly to mind

The last few levels of Super Meat Boy. Drove me absolutely insane, though when I finally beat it I was filled with a sense of euphoria ^_^ .... then I turned it off and never played it again . 

There was also the 15 min multi-man brawl in Super Smash Bros. Brawl... that annoyed the shit out of me. It was midnight when I tried it, so I just wanted to finish it before going to sleep. Every time the clock reached about 12 min, some idiot would throw a smart bomb or something stupid >_>. 

Oh God yeah, don't forget Yiazmat from FF12 and Alatreon from MHTri...

Good times