Griff should definitely give you the oranges quest if you ask him for quests, IMO. Making it so you have to talk to the elf in the cage instead is kind of counterintuitive, to me at least.
I'll disagree on this: The reward for finding Griff's supplies is that the elf will go free.If you never talk to the elves in the cave or cage, what would be your agreed-upon reward for taking on that quest from Griff? If you don't know about that elf, you have no interest in freeing him.
Tying the level of hints and direction with the difficulty could be a good alternative. Players like myself, who only want Tactician or higher, would get nothing and players who want more direction could go to classic or lower.
I'll disagree on this too. Combat and quests are different things. Tying quest hints to chosen level of combat difficulty doesn't make any sense. Just make the quest log more useful and ensure that clues you discover through dialogue are recorded in the QUEST, not only in a conversation log.