If you are looking for a bargain, good place to start is to look for bank owned homes. Please visit http://www.NaplesForeclosedHomes.com
If you are an handyman and looking to save $$$ on your new purchase, please visit http://HandymanHomes.Naples-Area.com
If you looking for homes priced below appraisal, for quick sale, visit http://www.NaplesHomesOnSale.com
Once you review those listings, I strongly recommend to sign up for automatic email updates, because best deals get sold first.
Feel free to contact me if yo have any questions.
Laimis Parseliunas, REALTOR
Signature Properties of Greater Florida, Inc.
1100 6th Ave South Suite 10
Naples, Fl 34102
Sand Castle Realty
It sounds like you are putting together a good plan and you are doing it at the right time. Some additional information would be helpful:
1. type of home, condo, villa, single family etc.
2. Approx. square footage
3. number of bedrooms & baths
4. Interests in golf, tennis, boating, theater etc.
Have you visited Naples? Do you have flexibility with the location? Are you planning a visit to the area in the near future?
Thank you for your post on Trulia.
The "Eckler Team"
Michael Saunders & Company
Scott is right; based on the specific zip codes you cite, the specifications you have outlined are going to be very difficult to find. There are other zip codes in Naples that are close to the beach (like 34110) that might offer some opportunities, but getting rent to cover the mortgage would be very tough. A small single family home here would rent for $1300-1800/month, depending on the size (and that would not be in the zip codes you outlined, but maybe in 34110). Rent could offset some of your expenses, but not all. Perhaps the depreciation of the property as a rental property could help make the numbers work better for you.
Let us know if we can help you more. I will email you some examples of homes in 34110 that might work.