Hi
You look like you are pretty well organised. What route are you taking?
DRs have been everywhere. Check out Mondo Enduro.
The best bit of advice I can offer is to travel light. I certainly wouldn't recommend having a backpack on for long distance travel especially when the tarmac runs out.
I would have thought that you can hire parachutes wherever there is a jump school. You have to trust them to have a safe plane so its not a big leap to trusting their parachutes. That said I can understand why you would want to have your own though.
You are the first parachuting motorcyclist that I have heard about so you may just have to go out there and find out for yourself what the issues will be!
Enjoy,
Niall
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