I'm doing a similar trip, I'm leaving late December. We plan on staying at cheap hostel/motels but will be taking camping gear just in case. I know that's a lot of shit to take but you never know. Also some of the places that you stay are so filthy you'll want to sleep in your bag. I can't help you with insurance but I'm going into this knowing if my bike is stolen or wrecked I'm out a $10,000 bike.
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