I'm wondering if anything like this exists or could be attempted. So when you buy gear in place A and need transport to place B you can advertise the job and how much you would be willing to pay.
Alternatively if you are traveling you could advertise your trip and pick up jobs for cash or even seats for traveller.
I know there are professional services that do this but I suspect you have more risk of crushed boards etc that way. And as far as insurance goes I recon its just a risk, just like with the pros. Trying to claim on damage is difficult if not useless.

Ive done quite a few really big drives to pick up special gear and though that if I could take someone elses stuff at the same time , that would be petrol money for example.
It would need to be a dedicated forum or would it even be a section on buy and sell. It can not go in a specific state as it needs to cover interstate travel.
Meeting other windsurfers is often fun too. And if you had a couple of jobs both ways it could start to pay for a holiday.

It would increase your boards value if transport options opened up. Means more buyers!
It could be done as the buyer owns the board in transit, and the sale difference is the payment. That takes the risk out for the buyer and puts it on the transporter. I'd expect a much bigger payment for that deal as it really is a form of insurance.
What do you think

If someone is already doing this a a job, let me know their contact.