Contact your local planning department for validation.

If a specific property has been identified, contact the planning department the property is located in and speak with a representative regarding vacation rental usages, when possible obtain the feedback in writing.

They really need to work on their communication, even between departments. 

I don't think we can expect at this price point the flooring to be like the vinyl you walk on in large department stores like walmart (those are commercial products)... but for the price, as long as you realize that there is a give and take, you'll be fine. 

The Department of Buildings said that if we state in the application that the Airbnb is part of our living space and not a separate space, then it'll be approved.

While the deal does not hinge on the ground-up phase, it could provide a significant upside.After consulting with the City Zoning Department and reviewing the dimensional regulations of the neighborhood district, it appears that my plan is feasible.

If you aren't comfortable talking to contractors, find a buddy that will join with you in that conversation - but be part of the discussion yourself.IMHO, $20,000 for the job as described would be great - if the contractor was quoting a price to the Department of Defense :)Note that if the sanitary sewer is on the other side of the street (and your sanitary lead is broken under the street), that's a different conversation.Best of luck!

When we went under contract with the actual owner (the daughter’s attorney contacted us), we closed on the property officially after redeeming the property on her behalf with the Sheriff’s department (she had a full year to redeem) and then the winning bidder received their 85K back from the Sherrif’s dept along with some interest owed.

Treasury Department and more, knowing about and looking the other way regarding the 2nd "borrower". 

To mitigate this risk you can meet with the zoning department before you buy it to confirm it is legally nonconforming but the lender could still be extra cautious.