I am a Canadian realtor who lives and works here in Sarasota. I also have some Canadian customers who are interested in renting out during the high season. They are looking for something from December 1 to March 31st. If you tell me a bit more about the condo, I could send the info to them and see what they think. One advantage of renting to Canadians directly is that they could pay you in Canadian dollars and no one would lose on the exchange.
Let me know if I can be of any help.
I suggest you call our company run property management company. They have years of experience with vacation property management. They will not be able to manage this property, but they might be able to direct you to a good company. You can find them on the web at http://www.cbcaliforniavacations.com
Can you tell me the rental policy (how often you can rent) of the complex where you are looking to purchase and any amenities that are offered, like full gulf views, tennis, etc.? This will mean a lot when finding the right vacation rental company to handle your unit. Many of the companies mentioned are highly reputable, however, each does specialize in specific types of rentals, i.e. weekly vacations verses executive relocations and annual rentals...
Again, best of luck to you and welcome to the Island!
Jim Soda 941-809-7759
Prudential Palms Realty
Sarasota-Lakewood Ranch-Longboat Key