Making Annoying But Never Stupid Games as a Challenge

[Steel Beast 6Beets]

On the other hand, one could put in some annoyance per-say.  I trust my colleague who penned the article would note how the game "Drakengard" wished to put the player through hell so he/she could experience Caim's descent into madness.

Drakengard is indeed a pretty hellish experience, mostly because the game is a poor's man Dynasty Warriors/mediocre Panzer Dragoon knockoff with all their flaws but none of their strengths.

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What about sidequests that are an intentionally obtuse and pointless but necessary to archive the true ending?

Nier, coincidentally from the same mind as Drakengard mentioned by VVulman, has the most demeaning, debasing sidequests I've ever seen in a game. The one that I always remember is "the Runaway Son" that requires you to travel all over the world on foot, no teleport in this game, pursuing a guy.

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You eventually return to the client's house only to find it empty. A nearby guard tells you that that family were con artists that borrowed money from everyone and then skipped town. And that his son wanted to escape from that life of crime until "some idiot" i.e you brought him back.

Also

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You don't get anything in return. Congratulations on wasting your time.