So I am one that you call an over analyzer and end up analysis paralysis; but I want this. It's all I talk about and thing about. The fear does stop me but I want to do this. So, I live in PA but really want to purchase a property in Florida. Especially in the area where my family and I love to stay. Kissimmee, FL. There is a real nice community that is still building to this day. I have asked for price of the different units they have. I asked if they work with agents; they told me yes but that I can but directly from them. Has anyone dealt with that? Also, do I need to apply for STR License in order to do short term rental in Florida and does me living in Pennsylvania have any effect in that? Also if any one can recommend a mortgage broker or any loan possibility where I can apply for the pre-approval and see how much I qualify for and I can see how the numbers work for me? Also, have anyone purchased a property thats not in a gated community and fixed it up and has turned it into a STR as well... Which way is the best to go as a first time rental investment for STR, buy a property in a gated community already built and ready to go or find a property (for a great deal) and rehab it and then turn it into an STR? I'm sure I will read different answers but I can't wait for the response. Thank you all for any help you may provide me. Like I said, fear is stopping me but I know I want to do this. - Jose M. ... PS also if anyone can recommend a great first time investor friendly agent would be great. Thanks again.