.- I had a conversation once in my owner's rep day job about new construction of a commercial building on its own parcel adjacent to another parcel owned by the same owner. 

Yes- I understand that as a wholesaler, occasionally you'll get massive checks, but as an agent, there is opportunity everywhere around you to rep people.

@Jack B.Check on the NIIT 3.8% if you are REPS that could be excluded but this may add other layers of complexity for other concerns with your tax planning you have a lot of fun stuff to work with.   

Real quick they tighten up and now welcome my team & I, or my rep, in. 

I have gotten mixed reviews and I am not sure the Airbnb rep understood my questioning (language barriers). 

Unless you qualify as a Real Estate Professional Status (REPS), you'd have same tax benefits rather it's in your current name or an LLC.

Very bad customer service and the sales rep lied to protect themselves.

I would get a second opinion from somebody other than the title insurance company rep providing you bad information.

I spent some time on a Zoom call with my VRBO rep going over it.

You will get a lot of reps in, build experience and local knowledge and capital and everything else will fall into place a lot easier if you are able to consistently find good deals.