There is enough land on the lot to build an additional set of 4 2 bedroom apartment units eventually so I'd like to look at cashflowing the original investment and then consider refinancing into a bigger build out later to create new apartments (rolling seller financing into it...).   

That person eventual backed out.

I feel like doing it this way will eventually catch up to you and you may lose EMD money or be sued for breach of contract. 

I'm planning on getting started with real estate and building my portfolio through rentals and eventually commercial property.

Eventually I would then hold some property in the SDIRA. 

I'd eventually plan to move purchase to an LLC but that's down the road. 

There were issues with noise from kids, late-night disturbances, and guests getting annoyed—too many factors you can’t control.I eventually shifted to single-family homes in Cape Cod, and that model has been much more effective and manageable.

I know technically it isn't smart, but I'm really hoping that playing the long game here will eventually pay off. 

That said the issues that are plaguing Airbnb and VRBO are only going to get worse as they continue to grow and will eventually lead to some harsh corrections and losses. 

Property with no clear ownership should be allowed to be used, and eventually owned, by someone willing to bring it into use.