@Armand Dufrane depending on where exactly your STR will be will help determine answers to your question. If you have beachside condo or an 8 bedroom near Disney will be much different. I focus on the Disney area and the homes here come already furnished and generally the future bookings will convey. The communities that I recommend are all within a 10 mile radius of Disney, are guard gated and fully amenitized, so they are built specifically for STR. There are plenty of smaller neighborhoods surrounding that allow STR or LTR that you could purchase if having a second exity strategy is important to you.
For your cash flow question, again depends on where you are and to what level your home stands out and what you offer that others can't/don't. As crowded as Orlando is with STR homes, we also have over 70 million people coming thru the city a year so even people not trying very hard are typically doing well. But if you do some homework, buy right and keep up the home and on your technology, you can do very well.
Switching from STR to LTR does seem inefficient, usually, you would go the other way to improve cash flow. However, having that as a plan is not a bad idea. When the pandemic hit, many STR owners turned them into LTR because travel halted and they just wanted to cover expenses at that point, others simply sold their units.
Best of luck to you.