We also are heavily invested in the Hilton Head market along with our clients owning multiple short-term rentals, long-term rentals, and now a new initiative in workforce housing.

Until then, my initial plan was to try and grow my capital (20k from a car flipping business) and get experience now so I can later focus more on cash flow down the line. 

AIrbnb's algorithm gives new listings an initial boost when you first list, so new bookings start coming in.

I'm lucky enough to be able to live with my parents rent free and with investing $600 into the property for 2 years after the initial year of ownership, I would end up saving around $30k.

Many MLS properties are initially listed for more than their true value.

I personally wouldn't go as far as to call them shady, but there's definitely been some fees and hurdles that weren't exactly laid out during the initial conversations and I'm in no way questioning your use of the description. 

The problem with rentals is not enough cash flow initially.

Note 2, historically initial cash flow has a poor correlation to actual cash flow.  

Even buying a $100,000 property wipes out almost everything and that's assuming you don't have to make any initial fixes/repairs.Retaining as much of your personal capital as possible should be a priority so that you can cover anything that may come up in your property or in your personal life. 

Hello,If I purchase a rental property in Miami this year and close under my name initially, and then transfer the title to a LLC the same year, do I need to anticipate TWO times the property tax hike for next year?