Here's H & R Block's flow chart for Airbnb/STR reporting: https://www.hrblock.com/tax-center/wp-content/uploads/2018/0...

Property Management always seems to provide challenging topics to explore :)  I agree with the others who aforementioned zoning considerations, water/electricity hook-ups needed.

You say it could cash-flow $1400 per month before expenses but as an investor you need more numbers.

My main goal here is cash flowing.

The typical investor profile is GenX or millennial individual or couple or a 1031X investor, seeking to maximize their working capital and cash flow.

Pay owner finance note for $200,000 and walk away with $200-$250k and still have a cash-flowing asset.

Even at a conservative rent rate, this thing will easily cash flow as is, all day, everyday starting on day 1 not on month 61 like your example.

I'm young and ready to take the risk If that means It will take years to cash flow I'm in for the long haul. 

Are you cash flowing the property?

Yale is great for student housing, traveling clinicians, and other cash flow ideas- not the fastest appreciation in the world, but getting better and the Yale impact as a behemoth "institution" isn't going anywhere :)