Will you be using the BP calculators (or alternative) to determine "pure" cash flow so you find a deal that really works.

A 1099 is just a report to the IRS, it does not determine if the amount is truly taxable. 

I understand that the current real estate is under-assessed and that the taxes will increase if we declare a higher property value, but this might be necessary.Can anyone give input on how to accurately determine the business value versus the property value.

That said, I wish you only the very best if you're determined to stay this course.

Determine what you are working with first for the roof and go from there.

In turn our revenue has increased by about 18% so far.In my opinion, your specific market and your pricing strategy are going to determine these statistics more than the overall sentiment about AirBnB or the other booking platforms.

Depending on the occupancy will determine the amount of down payment needed on the purchase. 

I think @Jeff S. nailed it.If you were determined to buy this I'd give some thought to a small office cluster for therapists/ practioners like counselors, massage therapists etc.

You need to determine a good time line.

In my experience, the insurance adjuster is the one who identifies damage and determines what needs to be repaired/replaced, then the roofer is hired to complete that work.