What challenges would you face if you had to support yourself by living off the island during colonial America

Food, water, and shelter would be the biggest concern if your still colonizing. If you don't have stuff like wood, or hunting gear shelter and food would be hard to obtain, if you don't have food, you die, and if you don't have shelter by winter, you die. Plus, you would have to stockpile water seeing as the water freezes over in the winter, so you'd have to keep it in a warm place as well, and being on your own makes all of the above a lot harder to do.

Dealing with a new environment,

learn how to adapt to the crops around,

and during this time there was a few tribes so if desperate times call for desperate measures possible request support, trade, or maybe raid they're camp,

from what I remember i believe to the first few who came to the new world a tribe helped the new comers to the island on how to plant certain crops, somewhere around 1620 or so