So, I'm looking to do a cash transfer or cheque payment to a Canadian man, for a VRBO townhouse rental ($500 deposit due now, $2500 rental change due late Feb).
Having read back into last year on this thread, I saw discussion of a similar problem, and the recommendation to attempt to go via paypal, for an approx 2.5% charge (which I assume was correct at the time).
However, I can advise that a paypal invoice issued in Canada for a bill in CAD will be charged at 2.9% plus a 1% surcharge for receiving a payment made from outside Canada/USA. This brings me to a fee of 3.9%. I would be looking to pay with my Citi prestige, so I would be adding ~3.3% forex fee, for a total of 7.2% (ouch). I would earn 3 and 1/3 KF or VFF points on the transaction, and would therefore be paying about 2.15cpp. Not great, but I would be covered by a credit card / paypal chargeback if the accommodation was not available / a fraudulent listing (unlikely because he has long positive feedback on VRBO).
The alternative is to transfer via Citi plus for a $20 charge for each transaction. This would cost about $170 dollars less, but there would be no purchase protection, and I would miss out on ~9000 points. I'm inclined to go via the paypal route.