I don't necessarily mind the way the challenges are set, but it does feel uninspiring having to replay challenges time and again for loot chases. Trouble is, there is no clear solution and I kinda feel bungie have done the best with what destiny is, but there could definitely be some improvements made.
In my opinion, the game balance for a long while is a sea saw... make it too easy and one side falls off, make it too hard the other side falls off. Over time players will keep falling away. There needs to be proper mid game to bridge the gap and encourage wider engagement (but that's just my opinion).
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The roadmap has very high expectations to meet.