Well the problem here is that Skyrim is so realistic that the bums spend all the money you give them on Skooma Beer wine Moon Sugar ext things like this. So they will always be poor and needing more money
I would also like to see this mode happen, even if it would get laggy. I have no Idea how to do this or I would just do it my self I used this mod when I played Oblivion so I know its possible I cant remember exactly how it worked tho.