There is a fine line though. If you make it to hard people will never run the content. As is it now, one wipe on a boss in LotA and 5+ people instantly leave.
Cape Westwind doesn't have any rewards.
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Are you joking? Ravana is the best thing to get in a roulette. Its a really fun fight, that is challenging but not too challenging. Wipes shouldn't be feared, and if the choices are faceroll or a couple of wipes for people to understand mechanics, then I say bring on the wipes.
To be instantly replaced by 5 more if my experience is anything to go by. Regardless, I'm not asking for hard content, I'm asking for the content to be its natural difficulty, so that mechanics are actually seen and people can enjoy the instance how it is actually supposed to be.
Trial roulette has rewards
Someone already mentioned this, but I think the ideal solution is to simply allow us to use all of our kit irrespective of item level, once we reach the appropriate level to use it.
I don't mind having my level lowered so that my base stats meet the criteria of a person who would be roughly at the correct level of the content, but the idea of having to suddenly lose everything I worked hard for sort of jibs me the wrong way.
Obviously item level would need to possibly synch'd down even harder to compensate from the extra damage a full kit provides, but hey -- I'll take that evil if it means not having that awkward transition when you're doing end-game content, but you're constantly having to reinforce bad gameplay/rotation habits because of level synch.