I see two things here. The first is that I am surprised that there are a lot of states in the USA where gambling is not legalised. Gambling has its bad things, like alcohol for example, but it is more than proven that by prohibiting it you don't eliminate it, you leave it in the hands of mafias and you stop collecting taxes. And this brings me to the second part, that part of the taxes will be used to help the homeless seems to me to be a poor argument. What we have to do is to attack the root of the problem and try to avoid, or at least reduce the percentage of homeless people.
Then, as for the clothes that people may be wearing, I consider that a secondary issue.
I actually see this a fight for old and new mafias.
Everybody likes the noble cause and if anyone oppose the Prop27, those guys will really look like a villain in the eyes of the society. The gaming tribes will definitely look like they are the ones preventing the advancement of the legalization measures. But both party have politicians on thier sides which I guess this is going ot be a numbers game.