I'm not sure why you would tie up your profit in a 1031 by selling.

and soil conditions can make owning rentals there NOT profitable for out of state investors. although with your down stroke you will most likely do fine..

One last point: It is important to ask if they have any limitation on the amount of profit spread between the A-B and B-C transaction.

It will be more profitable in the long run.Second, it sounds like you have focused on a geographic area in Florida.

Most beginners after their first year worry about how to deduct all their losses instead of how to reduce taxes on their (non-existent) profits. 

Assuming I don’t live here I would profit $483/mo from a $16k investment.

You can call some insurance companies to get actual quotes at any time, so a few phones calls can tell you if he is over paying. you also don't want to go completely cash poor to buy a deal, that's a tough gamble.

I'm the Campus Director at a local non-profit and my wife is an Occupational Therapist.  

When I find this out I think it indicates a seller needing OUT.So I ask  you, even though there are many of these houses in the higher price ranges, do you think the price of $300 K to about $1,5 mill is to high to make a profit ?  

Way to much work and problems.Best case scenario :  Find distress house and buy at 55% of fair market value....maybe 20% fix up and carrying costs and hope for 25% profit or less.But avoid junkers, heavy damage, roof problems, furnace problems, etc.