In addition to other comments from agents, I want to add that the price of the house and the home association fees will be a big factor in what your cash flow will be. You have to ask yourself:
Is the rent going to be high enough at one home to make it worth the higher price of a lower priced comparable home?
Which management company will provide the services I want and at what price/cut?
Is it in a location that will be desirable, or at least is the most desirable for the rental cost, which will stay occupied the most?
All of these questions and more are what you need to ask an agent and management company.
One gated community that has reasonable priced homes with low HOA and consistent renters (weekly and monthly) is Briarwood Subdivision. The community has a guard at the gate, and a 24 hr street patrol car. The HOA dues are $900, homes are in the $250s-$400,00s, and the community includes 2 pools, 2 tennis courts, playground, sand volleyball court, and basketball court. Many of the homes also have private pools. The rents are in the area of $1200/wk-$2000/wk (out of season) and $2100-$3000 (in season).
Let me know if you want any information and/or guidance!
Naples Realty Services, Inc.
Cell: 314-616-2313 (Missouri number, but live in Naples year-round)