How Jayel became the proprietor of the Wanton Wench is more or less a hand-waved affair by the local officials. The facts known by 'upstanding' folk are that a fresh-faced young girl by the name of Jayel came into Gatewatch, disappeared, and reappeared the aged and stern woman she is today. The facts known by the night watch are a marked decrease in drug trafficking and battered women appearing on the streets. The fact known by Jayel is that she killed a man with her bare hands, and has never looked back.
When was the last time a character caught a cold or flu? Real people get them every now and again even with solid heating and dry interiors. Your characters are out in the cold and wet, and even inside is not always dry and warm. Imagine having to stop your dungeon crawl, sitting in a tight defensive position, while you all are feverish.