Which hobo though? Lots of people in the slums appear to be hobos
You get the dream quest by sleeping in your condo's bed. As far as I know it's only there and somewhat random.
Okay, now I managed to get Arlene, the Hobos, Fawn, Sammy, and Lin Lin for help. However, whenever I beat the Don, no matter what way I go about it, I always get an 'ending.' The game specifies I don't really have a plan for what happens after I beat him. What do I do about that? How exactly do I get said 'plan?'