https://www.irs.gov/businesses/small-businesses-self-employed/tangible-property-final-regulations#SafeHarborElectionforSmallTaxpayersSafe Harbor Election for Small TaxpayersYou are not required to capitalize as an improvement, and therefore may be permitted to deduct, the costs of work performed on owned or leased buildings, e.g., repairs, maintenance, improvements or similar costs, that fall into the safe harbor election for small taxpayers.

First thing to do is google "City XYorZ Airbnb Regulations" and check into the legislation.

All of this revenue was earned prior to receiving qualification under Tier II of Regulation A, which expanded our offering cap from $20m per year to $50m.

Do they have to approve your tenants, what are the rules and regulations, etc ... 

He/you either need to study your state landlord tenant regulations or hire a lawyer.

We needed the survey to comply with zoning regulations and the contracts I talked to need initial plans before they will give me a quote.

This is illegal and highly regulated.

Bottom line, take the time now to learn your state landlord tenant regulations.

While it may seem asinine to you, the process has to be consistent throughout the portfolio and, the process is both regulated and enforced by both state and federal regulators....AKA the government.

However, I would recommend getting a second opinion from your CPA (partially because Treasury Regulations can change things, particularly definitions, even after we have the new law in the book).