Because he can put $1million on black at the casino and still have $1 million left when he loses.

You really do not need anything sophisticated if the arragement is a 50/50 investment. 

The kitchen and bathroom have been tastefully updated, and the inclusion of brand new stainless steel appliances adds a touch of sophistication.

I think the reality is that Airbnb is a larger company with a larger IT department so their software is more sophisticated and they have the staff to make software changes in a timely fashion to meet state and local laws.

However, for the seller to net the agreed price, the price has to go up in which case you can run into the issue of the property not appraising.I think the fundamental issue is this requires a more sophisticated buyer and seller (especially to have a graduated commission scheme which is common in commercial). 

Im not a very sophisticated investor like many in this group, but i just keep it simple does the rent cover my expenses and someday the tenants will pay this place off for me. 

Good idea, but the seller isn't sophisticated enough to do their own wrap.

I often reply with something like “thanks for reaching out but we are currently only working with more sophisticated investors and buyers”.

We are "Hollywood 2.0" thanks to Mark Wahlberg and have more businesses other than casinos coming in at a steady pace.

The folks I work with operate under the SEC exemption (I think Reg D 506b but I don't have it front of me) that allows up to 35 non-accredited investors, as long as they are sophisticated and have a pre-existing relationship with the sponsor.