My experience is that a big part of this industry runs on personality and being able to connect with people, and if you cannot do that you will be at a distinct disadvantage over others who can. 

This is imp distinction if you have both passive loss and income. 

I distinctly remember one advertised 3-plex where they said the annual expenses were something like $1800.

That would be correct if OP's father has made or intends to make an S election for the LLC.Since OP did not specify tax status of the SMLLC, we're left to assume no alternate election was made, and the LLC carries the default tax status: 'Disregarded Entity'.A DRE should not be issuing W-2s or 1099s to its owner as it's effectively dissolved for federal income tax purposes and there's no distinction between the owner and the LLC.

What we decided to do to comply with the city is to convert the home to a single family (removing one of the front doors), but keep the right side as a distinct space with a MIL suite with a small kitchenette and back entry. 

But the land is  common area even though there is a fence marking 2 distinct yards.

all three are distinctly different in form and function.roofstock is more of a MLS type system highly automated representing civilian sellers by and large and some turn key companies will list their stock on Roofstock.. its pretty snazzy however after care is between you and the PM.Homeunion has some hybrid of turnkey marketing company in the same vane as Jason Hartman Maverick Norada etc.MI is what many consider the gold standard in turn key investing.. very deep experience in the space.. and control all aspects..

The registry makes no distinction. 

You are correct that the tax treatment of Airbnb business (emphasis on "business") is distinct from other forms of real estate investment - and that you should get clarity about that to incorporate into tax planning and investment ROI analysis.

Stanley was fascinated by the different ways women get rich as opposed to the ways that men get rich.He believed that his research into millionaire women allowed him to separate them into two distinct groups, with minimal overlap -- women who got rich because they came from stable households that prepared them to become successful with money, and women from very different, unstable households who got rich in spite of the odds.