Welcome! And congrats on your plans - making the decision is the hard part!
You'll be spending a LOT of time reading, but here's the quick answers:
1: Insurance - generally yes, but some you need to have sorted before arrival. e.g. Canada / USA ideally in advance, you can't turn a wheel legally without it. EU of course you'll know you need a green card.
2: Shipping - there is a whole forum for discussion, and the base of information is the HU Shipping Database full of shipments already done by travellers. Mostly bike, but the shipper is either good or not and all can most likely do your van.
Start here for some shipping tips:
How to Ship Your Bike | Horizons Unlimited
and there's a link to the database there.
Be sure to browse the the menu system above - there's a ton of info and links to all the resources on the site - well worth a good read!
Have a great trip, and be sure to post about it on the 4 wheels forum!
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Grant Johnson
Seek, and ye shall find.
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Inspiring, Informing and Connecting travellers since 1997!
www.HorizonsUnlimited.com
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