I was asked how does one get their own squatter. It's simple really. We just happened to know ours.
I know a few homesteader's that will advertise for help. They trade work for room and board. Just remember that a lot of the people that will answer this type of job are running away from something, so be prepared to deal with those issues. You can look up to see if they have warrants, before allowing them to move onto your property.
I can't tell you what to look for. Sometimes your gut will let you know if you should allow this person to stay around, sometimes not. You want someone that is willing to work, not for money, but for food and shelter. Down times, like winter would be a great time for your help to get work, save up his or her money for extras during the long spring, summer and fall work schedule.
Make sure that you tell them the rules of your 'stead up front. Include everything, even common sense rules, from drinking, to if you expect them to attend church with you. You will also need a zero tolerance policy, and boot them out with any infraction. Just don't be hypersensitive, mistakes do happen.
There isn't medical help when it comes to this type of help. You can be up front about this, you can offer to help them seek out state help. Also remember that you will be required to pay for medical expenses should the help get hurt on your property.
It is just like someone apply for a regular job, make sure you interview well. Do all the necessary checks that make you feel comfortable. Other than that, be careful. Homestead help can be wonderful or a nightmare. Another option is look for urban dwellers that are interested in learning to homestead. You can get weekend help this way in exchange for canned goods, or a promise of living on property should things get really bad. (this topic will be covered more over on women not dabbling, long term Urban/suburban prep)