the AT is NOT the place to go find yourself for a few months, especially during the winter, and more especially when you are running very low, or out of cash. Plus weighing 300 pounds without recent hiking experience you aren't likely to last long on the trail
Spend several months planning, have several thousand dollars (3000-6000) saved up and do a real trip intelligently. I'd rec. the southern half of the trail though the smokies could be unpleasant in winter. also, maybe working on your writing skills abit?
david