I'm sure this game is fun, but i cannot bring myself to play it based simply on personal beleifs. I have quite a few friends who are either homeless or have been homeless, and i was cast out onto the street at age 15 by my alcoholic/ mentally ill parents.
The use of the word hobo as a derogatory term, and the stereotype of a homeless man as a drunk/drugged out social outcast is neither true nor fair to the masses of people who have legitimate medical/mental issues, or have simply chosen not to participate in mainstream society due to personal beliefs or experiences.
What you are doing here is much the same as blacksploitation movies or racial and ethnic stereotyping in the media. You are perpetuating hate, prejudice, ignorance, and suffering, and just because you grew up in the suburbs eating fucking cheesy poofs doesn't mean that you should make fun of those who are less well off.
perhaps you think this is no big deal, but consider how ignorant the average child is in america nowadays. Think about the fact that the next 12 year old to play this game will probably laugh and point at the next homeless person they see, and almost definitely ruin their day, if not drive them into further drug use/ seclusion from others. Just think about how you looked at media as a kid, and how little you questioned it when you were told something by the television or the internet. Given that you choose to mock the homeless as the main subject of this game, I should think that you have not done so.
I think you should go to the mirror and take a good long look at yourself, then really decide whether you think it is a good idea to keep these games up... I don't mean to make you feel bad, and im sure that you mean no harm in making this, but the idea that the poor and unfortunate are to be mocked is one which contributed, for instance, to the fall of the roman empire. I know you're just having a laugh, but you mus recognize that there are not enough honest, respectful, or wise people in this world, and you are just perpetuating and worsening the issue.