Hi AR,
I had two guitars shipped to me last week - both arrived in perfect condition. One was shipped in a Taylor box, with the form-fitting caps. The other was well packed with heavy-duty bubble wrap, the pillow bags, and all sides of the box lined with styrofoam. Definitely have it insured for the full amount.
You can use a credit card with PayPal and get some buyer's protection via the card. One of my transactions was with a Taylor dealer, well known on the forum. The other was an eBay purchase. There was also the eBay buyer's protection through that sale. Wasn't necessary.
Does the other individual have any web presence anywhere else (like on the AGF, eBay or a personal website)? I did buy a pedal from an individual on here shortly after I first signed on... smooth, easy transaction.
There is a leap of faith involved in any long-distance transaction. You have to go with your gut. A couple years ago, I sold a very nice Twin Reverb and extension speaker cabinet on consignment through a music store. We were heading out on an extended trip... I contacted the owner, was told the amp sold, and "the check is in the mail." FOUR TIMES. When I went back to the place, it was closed up and he was gone. I found him on the web, selling "custom guitars". A local newspaper had done an article on him and had a place for comments on their website. I posted my experience with the guy and immediately got a call from him. And then a cashier's check a few days later. It took me a "few days" to get around to letting the newspaper know that he had resolved the situation. Nobody wants bad PR... thus my reason for asking about any other web presence.
Good luck with the transaction. Keep us posted.
Best wishes,
Captain Jim