The biggest challenge or chore is Rogue. It’s perhaps good if you wish to research and exlore least painful ways of leveling with a gimped character.
I can’t see how it’d be any fun however. It’s not a class that’s a fun solo experience even when twinked.
I’d recommend paladin (cool quests and progression with items like deepwater harpoon, ghoulbane etc). Shadowknight also good. Ranger also has quite a few quests and fun stuff to try with track and whatnot.
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