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If I see a well-worn path starting at a random location along an isolated forest road I'm more likely to think "Marijuana Grow Operation" or "Meth Lab" than "Homeless Encampment". But still something to exercise caution about.
You also need to be a bit realistic. Homeless people and drug dealers don't like to walk more than most Americans, so usually their lairs are pretty close to a town or built-up area. So if you see a trail going off into the woods a dozen or more miles from the nearest habitation, chances are there aren't people living at the end of that trail. There are exceptions to that so I'd argue caution but not paranoia.
Another thing: if two streams come together and there is a flat spot nearby there will be a campsite. Usually a quite decent one that has been used for thousands of years. Similarly if there is an obvious ford of a large stream or river there will almost always be campsites near either side of the ford.
Interesting post for me. I camped at Harris a few years ago and can honestly say, that it is the only state park I was a bit uncomfortable in and it was largely because of the transient population. Fortunately, there were a number of other bike tourists in the hiker/biker site, so I felt relatively safe and didn't experience any problems. Had I been the only camper around, I would have been a bit uneasy. Just another symptom of the homeless problem in this country.