@Rob Ko I think most areas of winter park would be A/B. Good schools there and lots of development, money and high end establishments. Rents are high.
Celebration is also mostly A/B. The best part of Celebration is you are by Disney. You will always have lots of potential tenants and rents are high. Lots of growth and development around Disney.
Kissimmee I am not as familiar with in terms of neighborhood rating. But if I were to invest in Kissimmee I would probably target the 34744 zip code, north of East Lake Toho. I have driven through those neighborhoods and would say they are B/B+. This area is pretty close to Lake Nona and the Medical City. Tavistock is investing a ton of money into the development of Lake Nona. A mega town center is being built there as well as an Orlando sports district. Lots of high paying medical jobs. There is also an Amazon fulfillment center there, which is good for jobs. My wife and I reside in Lake Nona.
It's not easy finding a property cheap enough in any of these 3 markets to be cash flow positive, even with the high rents. If you see one on the MLS, you will need to act quickly, as competition will surely be high. Maybe finding something off market would be your best bet at a good deal.