Your desire to be close to the beach and or Olde Naples and within a good school district for a single family home under $300k greatly limits you from getting the best or even average ROI. For purely investment only, you get the best ROI from that property that rents well, but more importantly has the best potential for appreciation.
The Naples housing market is driven by second home buyers, not by local working couples with children in schools. Second home residents drive the economy. They are the economy. For investment, I personally favor properties that would appeal to a future second home buyer, but also would be desirable for an annual renter.
So with that criteria, it is then a matter of finding that property that can be purchased at the best price relatives to its true value. In other words, a great deal. In today's market, for any given price range there may be just a few or none available. But you are fortunate because you have a wide price range up to $300k.
There is no button in our MLS system that pulls up only the best deals. It takes a lot of work and research by agents that are very knowledgeable about the market dynamics, trends and Naples neighborhoods. Ones that have worked with many investors, and have purchase and sold many of their own properties. Come to think about it, that sounds like me.
Good deals get sold quickly. They do not stack up in inventory. But while good deals sell, other come to market.
Regarding the property for your own personal use, then you want the best value available fitting your personal criteria.
Find out a lot more about investing in Naples real estate here.
Glad to help