Do you have the painting in your possession? I had a problem with thinking I would pack and check a painting won in a New York auction, but it turned out that if I picked it up in person, I'd have to pay the sales tax. So I just had it shipped. You CAN carefully pack something like that and actually check it. It's basically getting the same abuse it would get from Fedex or UPS. But it would take some work. A packer will do it anywhere from $75-150.