JA, keep in mind that most of us can endure pretty severe hardship for a while, even get pretty used to it eventually. If you do have some difficulties and uncertainties up front, some rough months, or even a rough year or two, I hope you can look at that as the price of the ticket one pay for freedom and the opportunity to move toward better things.
Taking foolish chances is greatly overrated, especially when one gets older and in more questionable health. But there is not that much certainty these days in doing things the usual way either. At least if you are living a difficult life in a car or van, you have the opportunity to save money by living much rougher than most people could tolerate. Even though it's an opportunity you might hate, it's an opportunity to save up a financial cushion that you would not have if you kept renting somewhere ... always waiting for your rent to be raised, getting more and more attached to probably more and more things that you don't need and might hold you back.
I've been trying to train myself slowly to do with less and less. I'm losing battles all the time, but think I'm putting myself in the position to win the war. Don't let hardship put you off too much or for too long. A little of it is probably good for us ... and we might as well meet it on our own terms instead of having it come for us.