My 2 cents advise # 1: There are too many unknown about this OP's situation to give him a solid advise, so my advise to him is to consult with a financial adviser.
My 2 cents advise # 2: You summited Katahdin, and now what? In order to have a job, you need a place to live. In order to have a place to live, you need a job. Nobody is going to hire a homeless person, and nobody is going to rent or sell you a place to live if you don't have a job. So, unless you are a dependent, or you have a fat trust fund waiting for you, or you have some sort of income, one has to think about those things if you don't want to find yourself jobless and homeless at the end of your hike. Nice memories are not going to put food on your table.