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I flew to pick up my TBSS. Talked with the guy (private seller) a million times through PM, email, and phone. He texted me and emailed me a ton of pictures and videos. Any question I had he answered. At the end of the day I thought he was representing everything accurately and didn't seem like he was hiding anything.
Made arrangements for a flight after putting 500 in his paypal account. We agreed this would be refundable if the vehicle was not described accurately and actually had a very rudimentary contract drafted.
Guy picked me up at the airport and after I drove the vehicle around we went to his bank and exchanged payment / paperwork. I had a bill of sale and the license plate I was transferring on the vehicle and I acquired insurance at the bank and I set off for home.
It was a great experience, but also nerve wracking. You ARE driving a new vehicle miles and miles. For me it was a 1.5 day drive taking it easy. I got to know the vehicle well, and it didn't have any issues but there always could be something. Also all your states paperwork probably isn't going to be 100% done so there is a potential for something to come up if you get pulled over. In my case my license plate was still issued to a Red Camaro SS and a cop and I had a long discussion about why I was driving a Silver Trailblazer SS.
Either way, I'd do it again if the deal was solid enough or if I wanted a specific vehicle I saw online. Buying from a dealer may or may not be harder than buying from a private seller.
The guy that bought my Z06 flew in from New Jersey and I picked him up at the airport. I know that these are very specific vehicles, but sometimes flying is worth getting what you are specifically after. Especially vehicles no longer produced / specialty vehicles to begin with.
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