Florida should be busy currently with people staying in the Winter to get away from the cold & snow. 

I am looking to stay in the 250-350 range.

That encompasses realistically knowing what the market price of each unit is worth.Second: Stay in great neighborhoods.

Or just stay where you are with that current perspective that keeps you from being in the know.

Stay at it for 2 or 3 years and you will have your down payment 

You must give proper notice before each showing, you must give the renters the opportunity to buy the house first, and the new owner will have to honor their lease if they intend to stay.

I am torn between pricing rent lower with a minimum 3 night stay or just weeding out the less desirable/more work clients with higher pricing.  

By staying informed and adaptable, investors can find opportunities in both booming and challenging markets.Overall, with careful planning, thorough research, and a strategic mindset, real estate investing can be a fulfilling journey towards financial success and stability.

The goal is to have a place for us to stay when we visit his family (they live close to Torres Vedras) and also have a place that cash flows.

And, in my opinion, more importantly, the lurkers who never comment, now believe they have the "golden key" of information.As you already know, there is so much more to this, in order to stay out of trouble over the long term.