There are extensive threads on this in the archives.
Here are a few quick points. (I'm in Canada by the way)
Canada and the U.S.A. are each other's largest trading partners. Commercial buyers/sellers have the routine down pretty well. Generally speaking, problems are more likely to arise when you get inexperienced or unknowledgeable people involved in the process.
If everybody knows what they are doing, ther is no reason not to sell to a Canadian.
If people know what they're doing, the only difference an American should notice in selling to a Canadian is that they have to fill out a customs declaration form when the shipment is sent. (It's more complicated at the Canadian end but that's a different story)
So here's what "should" happen in a good transaction.
The American advertises on Audiogon. The price is advertised on Audiogon is in U.S. dollars.
The Canadian sends payment in U.S. dollars for whatever amount was negotiated: eg. price of product, shipping, etc., in whatever form was negotiated, eg. money order, paypal, etc.
Payment clears in the U.S.
The American ships the product in whatever way was negotiated, eg. postal service, Fedex, UPS (a.k.a. "oops"), wagon train, etc. (Well, maybe I was kidding about wagon trains to Canada. Obviously, you only use that for U.S. shipments from east of the Mississippi to California)
In shipping the product, the American has to fill out a customs declaration form. It will state the name and address of the buyer and seller, the value of the product and the country of manufacture.
The postal service, FedEx, UPS or wagon train delivers to the Canadian address.
The Canadian pays: (1) a brokerage fee to the shipper. If you use a premium shipping service, the brokerage is included in the shipping fee. If you use standard delivery service, it's a separate charge at the buyer's end. (2) duty, if the product is not covered by free trade. Duty is based on what the product is categorized as according to government duty schedules; (3) taxes to the government based upon the value of the goods as stated in the customs declaration.
All of these things have to be paid by the buyer before the shipper gives the package to the Canadian.
End of story.
So from the point of view of the American, the only thing that is different between selling to a Canadian and selling to another American is the necessity of completing a customs declaration form when shipping.
Now what can go wrong. Well, anything can go wrong. However, I will suggest three general things.
One is fraud, and that is no different whether you're selling domestically or internationally, although international fraud is harder for the average person to remedy. So make sure you have proper payment before shipping.
The second is shipping problems such as lost shipments or damage. This has nothing to do with the buyer or seller and is no more likely whether you're selling domestically or internationally. In fact, you're less likely to lose something when shipping internationally because there's more paperwork to trace something. And the Canadian authorities are very interested in tracing things since they collect tax on it! Damage, on the other hand, is partly a function of how much something is handled. Something may travel farther going across the U.S. domestically than to a place in Canada close to where you live. Going to Canada doesn't necessarily mean more damage.
The third set of problems are the buyer/seller problems, typically caused by the lack of knowledge or experience. This usually involves a lack of knowledge by the Canadian about the extra brokerage fees, duties and taxes. So they refuse to accept shipment and the shipper then looks to the American to charge back the brokerage fees.
In order to minimize problems when selling to a Canadian, make the points explicitly during negotiations. Tell them that the price is in U.S. dollars. (They're supposed to know but they may not) Tell them that they will be charged and are responsible for brokerage fees, duties and taxes and that these will be collected by the shipper upon delivery. It has nothing to do with you, the seller, and is an extra charge on top of the purchase/shipping price they paid to you. If they pay for a premium shipping service, brokerage fees would have been paid when the money for shipping was sent to you, so this could be eliminated. If the product was manufactured in North America, there would be no duty due to free trade. Otherwise, duty would be collected at the door. Taxes, however, are unavoidable in Canada. They will be charged this at the door.
If they know these things in advance, there are no surprises, so delivery should not be refused at the door. They would (should) have factored this in when deciding whether to purchase in the first place.
To get back to your original post:
Get payment in U.S. dollars. Let the Canadian do the money exchanging bit.
Ship cables with the postal service. It's quickest, cheapest and easiest.
Duties, if any, are not your problem.
Let the Canadian know he may have to pay extra brokerage, duties and taxes on top of what he paid you and that it will be collected upon delivery,... and does he still want to purchase taking these extra charges into account.
The brokerage fee is determined by the shipper. Tell the Canadian to consult with the shipper to find out what it is. He typically chooses the shipper.
Duties are fixed based upon the product category. It's unrelated to value or cost.
Taxes are based upon value, not original or resale price. The government will use the resale price as the value however, unless they suspect fraud. So it you ship a Levinson amp and say it's value is $100 in the customs declaration, you and the Canadian buyer better hope the customs officer is not an audiophile. They will see what may be a fraud and will charge the Canadian taxes on what they think the real value is. And then the FBI and the RCMP (in Canada) may suspect you're part of a larger smuggling operation and all of a sudden there's a wire tap on your phone.