Has anyone been able to get past Mama Bimbo? It seems no matter what I do whenever i return (even if I just leave and come back, that night has fallen and I go to bed only to get squished.

Yes. First time I got crushed by her, but then I just loaded a save from just before boarding the ship and did everything faster. There is a timer which starts ticking when you enter the boat and it seems that for some reason you have ran out of time.