Alright, I've figured out why you can hand-in the quest multiples times, so I'll have that fixed in the next patch. That shouldn't be the cause of your other issue though. So, you talked to Brittany, she left to go have fun with some Lizardmen, and then you talked to the purple haired girl, scared off the adventurer she was talking to, and accepted the quest from her, right? And you still don't have the "middle of nowhere dungeon" option in the outside locations teleporter? I haven't been able to replicate that, so I'm not entirely sure of the cause. My best suggestion would be to send me your save folder so I can check the variables directly and see if I can figure out the problem. You could post a link to it here—if you don't care about other people being able to download it—or you could private message me on TfGamesSite or F95Zone, since I don't think you can private message on itch.
As for the art, I hope to increase the speed at which I add more art sometime soon. I write new scenes faster than I commission them, at the moment.