Wikipedia agrees with Webster’s Dictionary: hobo is a term originating around 1890, meaning migratory worker or homeless vagabond. It goes on to say: “especially one who is penniless.”
For me, that’s the rub about Lynn Compton’s hobo dress-up fete. People can have a tendency to label others in a made up “us vs. them” system — if only “they” would stay in their own country, or if “they” would only get off the couch and government assistance and get a job. Conservatives certainly don’t have a lock on this subtle prejudice, but that kind of judgement appears to be more prevalent with “them” (see, I can even do it!).
The problem for many of us comes when satire or a lampoon is directed at a group that is perceived to be less powerful or less important than the satirist’s tribe. How likely would it be to see Compton and/or her handlers propose a shindig poking fun at investment bankers, political lobbyists, or even a roast of farm supply store owners? There are legions of migratory workers in South County, many I would guess struggle financially. “They” are also Compton’s potential constituents. Surely they deserve her respect.