Disney Steve,
Investing in real estate here is something that needs to be thought about for a long time.
Every week I shatter someone's dream of buying a home here because they haven't given the matter due consideration or they thought it was an easy investement. Too many folks have the same idea of buying a property, renting it out and hopefully covering the cost. It sounds easy but the reality is that it rarely happens.
I'm not saying it doesn't and I have a few successful people who do it, but it really takes a lot of effort and a little luck to succeed.
The questions you need to ask yourself are:
1. Why am I really buying the property ?
2. Who will use it ?
3. What are the costs involved beyond the mortgage ?
4. Is the property in the right location ?
5. Have I got time to devote to getting bookings ?
That's just 5 basic ones and there are many more.
Further, in this area you might be tempted by companies offering "rental guarantee schemes" and IMO they are not worth the paper they are written on. They sound all well and good but you try getting your money if they default ! Not easy.
Try and find a Realtor you feel happy working with and one that will have experience and knowledge in regard to the short term industry. There are a few good ones and loads of average/ poor ones.
The next step is to do plenty of research on existing condo's in the area and not just on Windsor Palms. Find out the average rental rates and occupancy levels. When you have done this ask yourself the question, can I still afford this if a) I don't get any rental income for 6mths and b) for 10 mths ?
When you are here in November, use that period to do plenty of research. Look at other properties including homes. Drive around the whole area and get a feel for the place. See what's for sale and generally take your time. I don't know if you have studied the market as yet but you should be compiling a list of properties that are for sale now and then seeing if they are still available when you come in November.
As far as the market is concerned at the moment homes in the price range of $140 - 190K are scarce. In 34747 zip code (that's Windsor Palms area) there are currently 229 properties for sale with 65 of them being condo's/townhouses. There are currently 5 properties for sale, all of them condo's/townhomes, from $ 124,900 to $ 185,000. 4 townhomes have sold recently from $ 119,050 to $ 161,810.
In 34746 area 259 properties are listed for sale with 109 properties not really in the right location for rental purposes. Lake Berkley seems to be the area with most townhomes for sale that woukld compare to Windsor Palms. Currently there are 13 townhomes/condos for sale ranging from $ 133,000 to $ 159,900.
The thing to remember in all of this is to take your time. property will still be here next year and the year after !