Maybe, but the boar king quest was implemented properly. You needa kill the boar king in the dungeon -- Eg either before the war event or after the war event -- As she'd be busy during it. Once you got the meat, take it to the old man by the bar and he'll tell you something, unlocking the option. With that out of the way, you're able to give her the right amount to play the event, which only runs when you're alone -- Otherwise you're rooming w/ the nun.
Don't even need the Skull flower, but that gives you an anal scene w/ her if you choose to lie/omit.
As for the not enough gold bit, yeah think dev copy&pasted that instead of having it lead to another text, such as you've already gifted her money or something like she won't accept any more.