When it comes to difficult games that fit my style of genre, then bring it on.
As an ex-hardcore gamer, if you can dominate in a difficult game, you just might acquire something out of it. Maybe big, too. Hell, if you were one of the first people to, say, beat I Wanna Be The Guy, you'll receive massive views on YouTube. If it isn't obvious enough, more people watch videos of crazy runs of any game compared to a casual run of any game. Why is this? Those types of gameplay can amuse and appeal to other viewers.
On my part, I'm mainly a bullet hell player. The most difficult game I played is Mushihimesama Futari...on ultra. Sadly, due to lack of save states (for the sole purpose of boss fight practices), I don't grind much. I do play the Touhou and DoDonPachi bullet hell games, and albeit I may not achieve as much as the past, at least it gives me something to do for an insane challenge.
Liu Kang ftw.
YouTube (mostly uploads of bullet hell shmups)
Clash of Clans = Town Hall 11, Level 151. Max balloons, max wizards, max P.E.K.K.A.'s, max golems, max witches, max valkyries, maxed base except for walls and heroes. Crimson Reborn fighting.