Long term strategy is to hold until it makes sense to sell, and that might be after only 2 years so I can reap the benefits without getting killed in taxes.

But, in future if we want to develop any residential or commercial buildings on this land, would this rail road track going to be a deal breaker in terms of attracting potential developers or buyers or investors? 

The plan is to short term rent some rooms, or mid-term, and live in the primary until its doing so well I have to move out and refocus on a previous renovation that has stopped until this one is complete.

Not sure how long the commute would be exactly but sometimes you have to sacrifice some comforts for long term goals.

Please include:When and how is rent to be paidWhen and how are utilities going to be paid (if any)When and how is the cleaning going to be (if shared or provided)What are the costs associated with damages / breaking stuff / calling a technicianWhat are the costs of breaking the lease, finding a replacement if you are doing short term leases on the roomsIf they lost their keys or check bounces what is the charge for it, how the cleaning of the common areas is going to work, and enforcing quiet hours.

We bought ourselves a furnished house with a giant pool, and also opened up a Short Term Rental.  

Things you want to consider would be what your long-term plans are with this property.

Brand new roof and each unit is good in terms of renovations. water heater from 2017. only concern is HVAC system is 14yr old, that’s the only potential cost that i see that could occur within the next 3-7yr.

My primary goal is long term appreciation and I'll accept a property that breaks even on cash flow.

Now, for long term rents I did not/would not pick it if the home is in Shaker Heights.