What's missing from much of this discussion is a real understanding of what the property is, ten acres in the heart of upstate New York Finger Lakes wine country, the desirability of that property as a vacation property on the one hand and the value of it as a vineyard on the other, and how local government (especially Yates County) is systematically trying to fight against the encroachment of moneyed OOS vacation-home buyers/STR operators  in the area.This is not some bland normal place where normal people live and operate.

From what I have seen from market research, it is a desirable area.

Highly desirable as a rental with the potential to convert the vacant lot to additional STR units.

If you can swing it and are willing to do what it takes to not lose the property if sh** hits the fan, then I would highly suggest purchasing in a more desirable area. 

The vetting process for serious leads may lead to the desired result.

What is your big desire with the STR loophole?

Of course we all want cash flow but if the property is in a very desirable area with a high probability of appreciating quickly over the next decade or so I'm fine breaking even or even paying a little out of pocket every month.

You can rent by the room, which can maximize rental income.Parent Guarantees: Many student leases involve co-signers, usually parents, which can provide additional financial security.Low Vacancy Rates: Due to the high demand, vacancy rates tend to be low, especially if the property is close to campus or in a desirable student neighborhood.Flexible Lease Terms: You can structure leases to fit the academic calendar, which means you can adjust rents annually based on market conditions.Cons:High Turnover: Students typically stay for shorter periods, leading to higher turnover rates.

Additionally, Millennials rely heavily on online platforms and mobile apps for property search, virtual tours, mortgage applications, and transaction management, reshaping the way real estate transactions are conducted.Delaying Homeownership and Embracing Renting: Despite their strong desire for homeownership, many Millennials face financial challenges, including student loan debt, stagnant wages, and high housing costs.

I wanted to start by house hacking but (1) I am not allowed due to strict HOA rules and (2) my city isn't as desired as the next city over.