North Naples is a growing community, close to Vanderbilt beach and just had the Mercato shopping center open. West of US 41 will pull a premium less than 6 miles to the beach at the 111 Immokolee exit.
Community fees are going to be high in golf communities and well manicured landscaping.
Rents have been in favor of renters with many condos on the market. Check out any restrictions in the communities to ensure you will be able to rent the unit you are seeking. Almost every community in Naples has golf so it will not be differentiated from most.
Most lenders in the loose lending days would restrict a home owner to 7. However these days many lenders will classify your purchase as an investment requiring more money down, slightly higher rates, and 6 months+ of asset reserves to cover all mortgages. 2nd home will only fly if this is your 2nd property or you can prove that the others are truly rentals. Banks will require bank statements and full tax returns, rental agreements on other homes if applicable.
If you have the income, cash reserves and the condo purchase is in no way a stretch for the next 3-5 years I would go for it. Naples is beautiful with extremely great golfing, close to the beach, luxurious appointments are standard in many communities.