Smoking should be outside, at least 15 feet from any window or door.

Quote from @Andrew Steffens: At 65 doors it is quality control and managing guest expectations.Yesterday someone threw a fit we do not provide snacks as they checked in at 4am and were hungry... 

I once had someone show up at 830 in the morning knocking on the door asking to be let in.

Assets identified in this study include:Permanent Fixtures: windows, doors, bathroom fixturesStructural Components: Roof construction, drywall, wood framingBuilding systems: water heater, electrical distribution, HVAC, plumbingInterior Construction: Wood flooring, stairs, ceramic tileThis engineering-based cost segregation study included the following methodology:Physical Inspection through a site visitDocumentation review including architectural plans, accounting records and construction documentsA cost analysis which utilizes engineering principles in order to allocate costs to their applicable asset classificationsCalculation of the depreciation schedule using MACRSAs a reminder, bonus depreciation started to phase out in 2023.

(For example, explain in your listing description or a message to the guest that you will email a door code at 9 AM EST on the day of check-in.)Vrbo’s actionsIf a guest contacts us within 72 hours of their check-in time because you didn’t provide information critical to their stay, we may take the following actions:Depending on the issue, we will either provide the necessary information or contact you for a resolution so the guest can proceed with their stay.If we’re unable to resolve the issue or reach you, we’ll cancel the booking, refund the guest, and help the guest find somewhere else to stay.

For a $300,000 property, this could be $6,000 to $15,000.Mortgage on Rental Property:Loan Amount: $240,000 (assuming 80% financed at 4% interest over 30 years).Monthly Payment: Approximately $1,145.Other Expenses:Property Taxes: Estimated at 1.5% of property value annually ($4,500).Insurance: Estimated at $1,500 annually.Maintenance: Estimated at 1% of property value annually ($3,000).Property Management Fees: Assuming 10% of monthly rental income ($2,400 annually if rent is $2,000 per month).Vacancy and Turnover Costs: 5% of annual rental income ($1,200).Total Initial Investment and Annual Operating ExpensesInitial Investment:Total Borrowed from Equity: $150,000Down Payment for Rental Property: $60,000Closing Costs for Rental Property: $10,500 (average)Total Initial Cash Outlay: $70,500 (initial investment from equity) + $10,500 (closing costs)Annual Operating Expenses:Property Taxes: $4,500Insurance: $1,500Maintenance: $3,000Property Management Fees: $2,400Vacancy and Turnover Costs: $1,200Total Operating Expenses: $12,600 annuallyExpected ReturnRental Income:Assuming $2,000 per month, annual rental income = $24,000.Net Operating Income (NOI):Annual Rental Income: $24,000Minus Annual Operating Expenses: $12,600NOI: $11,400Debt Service:Mortgage Payment on Rental Property: $1,145 monthly, $13,740 annually.Total Debt Service: $13,740 (rental property) + $8,592 (equity loan) = $22,332 annually.Net Cash Flow:NOI: $11,400Minus Debt Service: $22,332Net Cash Flow: -$10,932 annually (negative cash flow initially due to high debt service).Cash-on-Cash ReturnInitial Cash Investment: $70,500Net Cash Flow (first year): -$10,932Cash-on-Cash Return: Not applicable initially due to negative cash flow.Long-Term Appreciation and AdjustmentsProperty Appreciation:Assuming a 3% annual appreciation, the property value could increase by $9,000 annually.Rent Increases:Assuming a 2% annual rent increase, rental income will rise, improving cash flow. 

There is a very old door intercom and buzzer system that needs upgrading.

Even if he won't sign a new lease, I would simply post this on his door advising him of the new rental rate, take a picture of it, and save it for possible future need if you have to file for eviction. 

I have been watching prices rise over the last 6 years of living adjacent.

With rising values the assessment makes sense but the assessment raises seemed exorbitant.