I can say from experience that finding a lender with the terms you outlined will be very hard. 

The responsibilities you outlined are mainly what AirBnB itself highlights as possible co-host duties.

Truly appreciate the outline.

Your tenants must abide by the CC&R's and if they break those rules you are subject to fines that you must then try to collect from your tenants. 

He'll go out to the subject property and evaluate the roof.

Soon July 15th won't matter for when the subject property is closed.

The chances of them doing a short sale for someone who can afford the payments is between slim and none, and I'd take a wager it would be none.The better option is for the owner to sell the house to you on Seller Financing or Subject To.

(I know 'best' is subjective but I want to hear everyone's thoughts and why they like their strategy & believe their strategy is the recommended for the long run.)So far the most common one I know is to focus on sing family house, pay 20% down, and rent it out, and do it over and over again.

And thank you for outlining a view point opposite everyone so that I sort of see both sides of the coin.  

Not sure how to go about doing that for a piece of land - probably the same steps i've outlined above?