WTF is this mess? I'm confused. So, you are going to walk to BC, you're fucked in the head and body and..... ? Why exactly are you... doing whatever it is that you are doing?
If you don't want to go to college or film school, fine. Go to a trade school and learn an honorable trade. That way if you decide to hit the road you will be able to eat along the way. Chances are (although not 100%) your stomach problems are due to stress and diet. If you drink coffee, stop for six months. Try not to stress over stuff and enjoy learning a trade (You can go back to college later). Then enjoy life. Not everyone is a Buddha and thinks they know the meaning of life, but that shouldn't keep you from enjoying it. I did sort of what you are proposing, but that was a different era. Times have changed and I don't think it would be a good idea now. Trying it in winter would be even more fooloish.
I wish you the best of luck friend. It might be to late to say goodbye It might be to late to watch this sick old city die Going on the road, yeah I'm gonna try Sick city so long good bye and die.