@silverpinups wrote:
Will there be an Insurance or Mailing issue if I don't have my full address on the package?
This is something you could check with Canada Post, but I would think so, if only for your own peace of mind in the event of a "return to sender" scenario.
If I may, it strikes me that you might be over-thinking this potential sale. Bear in mind that the buyer is willing to spend a fair amount of money on an expensive item and will have to trust you as well. You both have to step over that threshold a little.
Why not do this the old-fashioned way if the buyer's location is within driving distance? That is, deliver the item personally (take a friend along for moral support and security) but set the terms as either Paypal payment or certified cheque. I expect the buyer would be both impressed and pleased with such personal delivery service. Many galleries still do this for important works.
Rather than a coffee shop, consider meeting in the lobby of the buyer's building if it's a larger office building. Usually there are a lot of people coming and going in such places. A coffee shop is probably next best. I wouldn't suggest a police station in this instance -- it does suggest a certain mistrust of the buyer, or at least nervousness about the transaction.
Go prepared with (another old-fashioned idea) a duplicate printed receipt you create in advance for the buyer's signature, confirming the buyer has inspected and received the painting in satisfactory condition. It doesn't have to be an elaborate document -- one paragraph of text, along with the purchase price, payment type, date, a signature line, and your business name/logo and email address somewhere on the document will do. Make sure you have the buyer's full name and contact information included. If you still feel concerned, plan to have your friend take a photograph of the hand-over of the painting.
Give the buyer one signed copy of the receipt, and keep the other for your records (and protection against SNAD). This is still how transactions of major items like vehicles and houses are conducted all the time, and in fact many delivered-to-the-door major consumer goods like furniture, appliances, etc. The customer is usually asked to sign a "received in good order" bill of lading.
Lastly, if this is a framed painting (is it under glass?), in my view the risk of damage during transit with Canada Post is far greater than the small risk you might take in transacting this exchange in person.
Even if it's a rolled canvas being shipped in a tube, I'd be more concerned about all the handling through the postal facilities than I would about showing up with it in person. And in person there is no need to provide your home address if you prefer not to. You can confirm Paypal payment (or certified cheque payment) on the spot, and the buyer gets their painting immediately. Neither you nor the buyer have to worry about the time it takes to be delivered or the condition in which it will arrive.
People tend to forget that everyday business was conducted like this quite successfully long before the internet arrived. There is no reason to think this shouldn't turn out well, given a bit of forethought for your own protection, as well as understanding of the buyer's position. Congratulations in advance, and I'm sure this will be a happy ending for both you and the buyer!
