@Matt I.I suspect that if you are not getting bookings (airbnb or off platform) his other clients are not either.

I also suspect she waited to the 11th hour intentionally in hopes we would still use her with worse terms. 

If so, (I suspect that will be yes) you should add them as an Additional Named Insured on the the policy.You mention later that you have Umbrella policy.  

A few years later, decided to replace the cement walkway that surrounded the perimeter of the house, widening it, which  suspected was another source of the flooding, had the walkway angled out, so rain water would flow away from the house.

Some rent history will help as well as I suspect you may have.I'm surprised there are not a lot of comments in here moments after the post :)  The good news is there are plenty of lenders for this your scenario. 

I suspect you'll have a difficult time working with these lenders just based on your price-point, most are going to start on a $100k minimum loan size. but just food for thought -- how it works is: instead of looking at you as the borrower and your "ability to repay" the mortgage, they look at the property as a business.

I suspect you can learn everything they offer by reading BP and some good books.

But I suspect you would have roughly the same mortgage payment of around $3300 but you could rent each side out for about $1500 side for a total of $3000 monthly.  

If I had the choice between owning a dumpy property in a suspect area and buying stocks I would buy the stock.Works for me 24/7 and no tenant headache.

I suspect this might be a reason you have not taken that first step.