A possible solution/alternative to the current challenge reroll system is to arrange them into pools tailored to various playstyles. Something like:

1) Grouped or high-level content (Trials, Arenas, Dungeons)
2) PvP (Cyrodiil, Imperial City, Battlegrounds, Duels)
3) Overland (harvesting, kill X critters, WB, antiquities, quests)
4) Thieving /Stealth (pickpocket, treasure chests, thieves troves, sneaking, being invisible)
5) New Players (Mount training, trait research, level ups)
6) Aesthetics (Housing, outfits, emotes)

I feel there's an opportunity here to include more roleplaying aspects too:

7) Good-aligned (healing X damage, donating X gold or Crown store items to other players)
8) Evil-aligned (Dark Brotherhood, killing innocents, vampire feeding)

Additionally, some challenges could overlap several categories or be global, such as crafting.

From these, we would then be given the option to choose which pools we like the most (perhaps a minimum of 2-3 to enforce some variety) to roll challenges from, excluding the others. That way everyone should get to do what they like most in the game and not have to worry about getting unsuitable content. If you wanted, you could pick all of the pools, of course.

This system would also open up for a greater variety of individual challenges to choose from in each pool. I'm sure we can all think up a lot more of them than I suggested here.


A minor comment: Including antiquities challenges at this point seems unfair to players who don't own Greymoor as they literally cannot complete them.