I wouldn't worry about it myself,..if the tow vehicle and trailer are in good working order just send it,...
If you are worried about your friend moving the car , and all the talk about insurance and extra policies to cover it , Just hire a professional transporter . East coast is a major route for them . I'm sure it can be done for around $600-$700 . Worth it for the peace of mind .
Sounds like you need to get coverage on the car anyway. I'm pretty sure haggerty offers project insurance that is pretty cheap.
My truck ins covers whats on my trailer. Have ins on the trailer through the same commercial company that insures my truck and I have classic car ins on the Riv and Wildcat. I should be well covered for anything I haul. If I was your shoes , just make sure you have ins on the car before he loads it. Classic coverage is cheap.
What I meant Brad is for him to have his friend take out the extra polices on the trailer etc. he make the payment for it and once the vehicle arrives get his friend to cancel the extra polices. However like others stated it's probably less hassle to have an actual company ship it. Best plan is for him to haul it himself that way if anything goes wrong he only has himself to be mad at.
Through our commercial insurance we had an issue with trailers, we had to but extra insurance for them. So the the trailer is covered by the tow vehicle as discussed in this post. My insurance carrier told us if something happens and the trailer has to be left on the side of the road...disconnected from the tow vehicle and someone runs into the trailer the tow vehicle won't cover the trailer sitting there by itself. .uggg