You have a cool dad! 
Ha ha cheers vdk!
Well it was a good idea artic until you started down the insurance fraud bit, sorry but that's just not me. I think rental is the safer (and slightly more honest) option.
Well it was a good idea artic until you started down the insurance fraud bit,You have a poor understanding of law. It's not fraud and it's not illegal. In the worst case scenario, that involving a teenage driver, it would be a breach of contract. It's no different then letting someone else drive your car providing they have the legal right to drive and are of the same age risk. I swap bikes with many ppl over 30 years of age and it's perfectly within my insurance contract to do that without notifying each time.
Suit yourself, but renting has so many restrictions and hassles it would take the leisure out of it. I looked at that Toronto rental place and with mileage penalty it's about 2K per week. That would be 8K for the month plus 3K in deposit. That's whack. Personally I'd lay out the short term cash and have a bike waiting so he could go where he wants and dump it anywhere if need be.
As I mention you can notify them that your dad will be an occasional with an international motorcycle driver's license if you like all your I's doted.

It won't make any difference to them. The biggest issue is getting any money back on a policy cancellation. In the good ole days one used to get a policy, ride for 4 months and then cancel the policy. Now they want the full year.