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Since winter is coming I suggest getting your ass to the south asap. If you find a small rich white community, a creek and a place to sleep off the beaten path you can do quite well. Hit up food banks, community centres for lunches, dumpster diving, foodstamps. Learn to make fires easily, have a small pot for cooking. Buy rice, eggs milk (just enough so you can drink it before it goes bad)
Do as many good deeds for others as you can and be as selfless as possible, scrounging never helped anyone. This karma shit is real on the road, I've had so many near impossible great situations come up out of nowhere that saved my life or just brought me extreme comfort after hard nights that I don't think would have happened if I wasn't trying to be as charitable, helpful, honest and cheerful as possible. Be the dharma bum. Meditate n shit, eat healthy, get a nice tent - sometimes they give them away at catholic church's. Look for outreach groups that are there to help people like you, be grateful, they enjoy giving as much as you enjoy receiving.
It's a lot of fun but can be tiring after a while, I wouldn't be surprised if you take out another loan and go back to MIT after a few months on the road. It isn't glamorous and is filled with a lot of discomfort. Learn to dry out your clothes quickly by ringing them well, only wear wool socks, dry shoes by the fire, bring bandaids, moleskin and polysporin for blisters. Carry salt with you at all times. Chia seeds are a great meal replacement, just mix them in a water bottle with some sugar and you can go all day.
Multiple hand towels are great, I prefer that over one big towel. Do you have a rain cover for your bag? Do you have at least one dry sack? Do you have a pair of flipflops to tie outside your bag? Do you have tarp and a rope (double shelter is better than just tent)?
Do you know how to make a fire? Do you have the tools to do so? Do you have a good destination that won't be too harshly effected by winter climate?