You don’t see this in syndication books because it’s not typically a syndication sponsor’s function.  

It tracks well with what I have heard from some Airbnb specific managers in my area and was so easy to use (the free functionality, I haven't messed around with the paid stuff).

I have several SFR's that I manage using Cozy....I am happy with the functionality for my needs to this point.

The BEST way to protect yourself is to know the law, obey the law, ensure the property is safe and functional, and treat people honestly and fairly.2.

However, you very well could be sued for refusing to rent an upstairs unit to someone because YOU didn't believe they had the necessary mobility/functionality to live in an upstairs unit. 

Snow plowing services are in high demand all across the country right now, ok minus FL and CA maybe.If you're a contractor with some pickup trucks it may be very tempting to offer that, as you may not be able to do your regular work on snow days anyway.However many GL policies may have a "Snow plowing operations exclusion" or a "Classification limitation Endorsement" meaning only the classes of work specified in the declarations are covered.So if you're a Contractor wanting to or actually offering Snow plowing services give your agent a call and see if your policy includes snow plowing operations or if it can be added.And if you're a property owner hiring your favorite Contractor to plow your property don't just rely on a certificate of insurance ask for it to specify snow plowing operations or review their actual policy to verify snow plowing isn't excluded.

I would take the time to clarify expectations in writing and also to make an agreement for what you all believe should happen if for any reason he is unwilling or unable to fulfill this function in the future. 

Appreciation is largely a function of time.

While some of these buildings fails in high winds and huge snowloads, that's more of a function of engineering.

I would venture your best preparation for this type of venture is to actually work at one and gain insight to how they function.