While housing is a need everyone has, Vermont in no way has ever been an easy place to live back to colonial times, expecting others to pay for fresh transplants housing is bullshit. There are plenty of states where you can survive year round outside if you don't want to work for a living. Vermont however isn't one of them, and yes you should suffer the consequences of your actions where if you are a shit person with no marketable skill to survive you do not belong here and if you try the elements will kill you. Try somewhere easy like the Carolinas, Virginias, Tennessee, Kentucky, Georgia, Alabama, or Florida. Those are all places you can be a vagrant all year long and survive.