Secondly, if this strategy qualifies for the STR loophole, would I further be able to run a cost segregation study on the unit that I plan to STR, in order to take advantage of bonus depreciation? 

While I have not studied to determine if the Orlando market is saturated I can atest there is alot more than Disney. 

I've been studying my butt off, but now that it's happening, I feel lost.

Study your competitions, see how you can offer more values to your guests.

The interesting thing is when we drove around the area, the houses weren't in any particular "style" -- one looked to be like a classic large ski chalet, another was a different type.

Everyone is just gonna name random cities, but the answer is study your own market and figure out and this is gonna be subjective where there is “value” there is no exact formula or data for this, but if you live in place it should be somewhat easy, what neighborhood’s seem like you know that price isn’t so bad for what you are getting or conversely that area seems really overpriced for what it is.   

We also put some gaming chairs and a couch and a table for classic style Families love this set up because they can leave the kids in the game room and then have fun playing on the pool table or other parts of the house that they’re younger children playing in the game room a mini split to help with temperature control and get really cold at night and really hot in the afternoon in the summertime.

Currently, with your layoff situation, you have the opportunity to concentrate on market analysis, studying trends, rental needs, property values, and potential value growth.

Purchase price: $1,345,000 Cash invested: $500,000 Sale price: $1,825,000 Case Study: 3142 Fairfield AvenueThis case study delves into the transformation of an 8-unit mixed-use property, a blend of residential and retail spaces, located in the vibrant Black Rock neighborhood of Bridgeport, Connecticut.

I suggest studying everything first considering the risk and your resources.