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 :) 

Are you looking to cash flow now or wait it out (with less cash flow) using a loan or owner financing? 

I would be happy to show you several cash flowing properties in the City proper so you can see how this works.

@Anthony WilhiteIt's fantastic that you're diving into real estate investing at such a young age, and it's great that you're starting with valuable resources like "Rich Dad, Poor Dad" and books from BiggerPockets.Here are a few tips and considerations as you begin your real estate journey:Make a calculated financial plan.

You can get a $400,000 property to cash flow.

Every investor’s goals, resources, and strategy are different, and there is no one-size-fits all solution to market finding.You’ll walk out understanding:How to balance your goals for cash flow and appreciationWhy home prices don’t paint the whole picture for affordabilityHow metrics like the rent-to-income and rent-to-price ratios are similar (and how they aren’t!)

The advantage is you get greater returns in terms of cash flow.