I had my wife's truck shipped when I bought it. $1,300 for a fully insured shipment with residential pickup. They put her 80 on top of the carier backwards and ran it through a tree. $1,700 in paint & trim damage that I have had fixed. I'm still fighting with the shipper to pay for the damages. $3,000 out of pocket at this point. We love the truck, wouldn't trade it and would have been willing to spend $3K more for it than what we did. Still, shipping sucks. I kick myself over and over for not simply buying a one way first class ticket and driving it back 2800 miles staying in 4 star hotels. It would have been about the same cost. The truck was her mother's day gift this year. Supposedly the shipper has a check in the mail to me for just under $1500 to cover the damages. So far it has spent a week in the mail.
If you're nervous about towing one behind the other don't. Drive one out, fly back, drive the other one out. If you care about your vehicle don't ship it. The $500 'bargain' shipping is the uninsured rate. The fully insured rate is going to be closer to $1000. If you want it picked up from your house add ~$250-$300. If you want to be able to pick it up from the destination terminal on a weekend, add another $50.
Fill them full of your stuff. Drive them out one at a time. Put one in a storage rental if you need to delay fetching it.
From my experience shipping was a major PITA. I'd rather do a fleet of PHHs than have to ship one of these again.
