Rural town but within walking distance to an elementary school, a high school and a nice restaurant.

If one or more units are vacant, the remaining units often don’t provide enough cash flow to cover expenses, making it harder to meet operating costs.Maintenance costs: A fourplex comes with four times the appliances, plumbing, HVAC systems, and other components to maintain, leading to significantly higher repair and maintenance expenses than single-family homes.If you want to see the detailed calculation, read this BP blog - More Units Doesn’t Mean More Money—Why a Single-Family Home Can Beat a Fourplex.Resale value: Multi-family properties have a limited buyer pool—mainly investors—who base their offers on CAP rates.

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

Weather cools, people are busy with school, resting from summer, prepping for the holidays, etc.

Most folks are charging 10% of the rental rate for monthly PM fees. 1 months rent for a leasing fee and couple hundred for a lease renewal.

With interest rates where they are, that could keep your cash flow strong while allowing you to scale. 

They told him, “We need more 3-bedroom homes near schools.”

Not really interest rate returns..

Pay market price, BUT with seller financing, or assumable financing, at a LOW interest rate.

Since we pay taxes in arrears, the appeal process must move along quickly as they are payable in November (at a discounted rate).