I live in northern Virginia which is part of the DC metro. It is an expensive market and very hard to cashflow. I wanted to invest in other states, like Florida, but I felt nervous about long-distance investing. Hence, I decided to search within Virginia and bought two long-term properties in Hampton Roads (one in Virginia Beach and one in Chesapeake) last year. It is a 3.5-hour drive away. I rely on a professional property manager on these tenant-occupied properties she already has been managed. But, I know if something goes wrong, I can get down there relatively easily. One year later, I now feel more comfortable with long-distance investing, and am branching out to Jacksonville. I took a trip to JAX early this month and am likely to invest there. Since you already live in FL, you have an advantage than all others like me trying to get into FL markets. This will narrow down your search quite a lot. After observing the market a bit and doing deal analyses over time, you will be able to identify deals that work for your criteria. Good luck on purchasing your first investment property!