I live in a beach town in Florida. We have tourists year round. Most people stay a week or two, then go home. They would not notice anyone staying for a long period of time. It would be very easy to blend in with tourists.... straw hat, sunglasses, etc. because everyone is dressed that way. This time of year our homeless population doubles or triples because it's warm in the winter. I know this because I volunteer at a free food pantry/clothing bank. Food and clothing would not be a problem and, if he disguised himself, he probably wouldn't be recognized. I don't believe he left the state of Florida. He doesn't have to worry about the climate so housing wouldn't be as big a deal as a colder place. There is literally water everywhere, so he can fish or scallop for food. He might not be as comfy as he would be at home, but he wouldn't be miserable. This is just my opinion.
edited by me--I haven't posted before and I think I replied to the wrong post. I meant to reply to the one about being on a beach somewhere.