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After you rest in the rookery for the first time, I believe your health should go back to full. That makes sense to me and would reduce the need to have use some of your healing.
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Let the challenges be retroactive. I enchanted a piece of gear, spending some of my only coin. Right after I go to see there are challenges that ask me to go enchant a weapon… Maybe if it’s already been done we can have the challenge be checked off without having to do it again? I think the challenge disappeared as well once I “abandoned” it.