That house has returned all my initial investment and going on double the initial investment.

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. 

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.

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.

I need to shift now to having practice sessions in doing research and in watching auctions online.

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