Get licensed with a broker who will support your investing goals. 

Booking.com is awful. 0 support yet they take the same or more as other platforms. airbnb and vrbo should be more than enough.

I have tried everything to get the tenant to complete the assistance formalities - started their  application, filled out most, but it still needs supporting documents to be sent directly by tenant, which they are not doing and not communicating. 

I have about $30K of cash ready to use to support.

The current FAQs indicate one can stay over their max allotment of 44 nights provided there is scheduling availability but there is a premium fee to pay to do so (sample fee cost not provided).But I assume Pacaso doesn't do such offering as it probably makes the management and mathematics a pain to support the scheduling and ownership with so many owners for one property (26-52).

The room is raised foundation as it is above ground but has slab to support it.Definitely agree, this is why we are doing as much research as possible before renovating. 

Also decided to put some boulders for shoulder support and for aesthetics. 

huh... think about that...But, as you mentioned, if you don't have the income to support the increased loan amount at the available terms, then you don't qualify and this isn't an option for you. 

In the 1980's there were numerous robberies in the area, so I told him to ditch the laundry and collect store rents instead.

If you support your parents over a certain %, that is a tax write off.