I am in my 30's and am interested in buying a condo (would consider a
home or townhouse as well) in SW Florida to rent out. What are some of
the top areas (3-5) that you would suggest given my objective of:
1) Renting out the unit 85% of the time so I could try to cash flow
the purchase of the proprety (i.e. pay all expenses with the rental
income), and
2) Gain solid appreciation over the next 5-10 years.

I can't spend more than $500,000 and would prefer to be in the
$200,000-400,000 price range. The condo must be at least two bedrooms
and on or very near a beach, again, with an environment (family
friendly) that is very attractive to renters. I am curious if it's
better to save $$$ and buy a place across the street from the beach or
to go all out and buy on the beachfront directly.

I have looked at St. Pete/Clearwater on south down to Sanibel (and
Siesta Key/Bradenton/etc. in between). These areas are fine and I
would be interested in hearing about them as recommendations but would
also want to know some of the more obscure/smaller/up and coming areas
as well.

While I am not really interested in anything North of St. Pete, I
wouldn't mind hearing one or two recommendations on real "up and
comers" throughout the pandhandle. In order to really answer the
question I need to best know the different areas to target to begin
looking at properties given my price range and objectives. If you
would like to include any information such as: rental management
companies in the area, recommended realtors, or rental units that
would be fine...however, I really want to know most about 3-5
different recommended areas of SW Florida to buy a rental unit and
also "WHY" you would recommend these areas.

I don't have an answer for you, but have you looked into the North
Port/Port Charlotte area?  Both are not too far from the beach. Siesta
key is a high $$$ area.  Some place between Sarasota and Ft. Myers may
be a good place to look...just a suggestion...good luck!!