You should contact MD and see if they can hold it for you until you get back (sign papers saying as much)
1. Once shipped the best tracker besides the shipping company in possession of your truck will be your dealer, not the factory.
2. If I was you, I would try to go through Chrysler Capital first for any incentive there may be, and then turn around and go to PenFed if that's an option for you.
2.1 If the above is not an option, PenFed should allow you to use the app, call, or go in person (prefered) to apply for a loan and see how much they give you. Loans should be printable same day at whatever PenFed location you go to, If they give you a loan for more than the truck is worth, whatever isn't used will go back to PenFed.
3. Not sure I completely understand this question so I'll try to answer. (StateFarm experience for me) Insurance should be able to be taken care of day of purchase. For me I'm purchasing in a different state than where my tag is located (my tag and insurance are same state) I'm sorry if this isn't much help, calling your insurance company and asking them questions will be the better route here.