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What I can't get a handle on is occupancy on places, how long the season is (do they still rent in September at the peak of the 'cane season?), and the like. Any advice on how to research an area's vacation rental market, or advice on screening realtors for one that's going to be straight with you?

Go to the listing websites and look at the calenders of the properties in the area you are interested in. Some are better for this than others, as some gray out days that have already gone by. HomeAway and VRBO require a considerable amount of tracking, VacationRentals411, if they service your area, allow you to look back and get a full year picture. Another way could be to talk to a management co, let them know you are interested in buying and will need a manager, (IIRC, it's a requirement, at least in certain parts of FL,) and ask them to show you the actual data for similar properties to that you are looking for. Ask them for a Realtor as least it is a starting point. I'm not sure what you fear they won't be straight with you about, but then in my area Realtors have the saying "be the source of the source, but never the source." It's way to litigious up here.

It's not a small amount of time, and you will soon realize that some people simply don't update their calenders. Others take it off the market for part of the time, so look for days here and there between filled weeks to see if the place is actually active. Or it could be a longer term rental. Pretty soon you will narrow the calenders down to a few that you have confidence in.

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