.- Planning to buy and hold for multiple years and initially check if it really cash flows (and passively) or notMy Concerns/Questions- The property is 1939 so what if big expense like HVAC or Roof comes up in few years?

Smaller homes are slightly less profitable, since certain items are baseline regardless of home size (i.e. roof replacement baseline, 200 amp service, etc) and the spread on wrecks is not that great from a smaller to a larger home. 

You mentioned it has been on the market a while - is the roof/furnace/appliances/water heater/etc etc nearing end of life?

Seeing as how I assume you would never have the major expense of replacing a roof or maybe even an HVAC system as some high rises may not have individual HVAC units for each apartment it seems you could allot less to this.

Since they are not constructed well as house they are prone to lots of repairs Iike plumbing that is made with PEX tubing and roof seams that leak if not caulked with urethane or silicon every year.

They tend to leak and when water infiltrates the roof seams the water will  travel down inside the walls and when the water freezes the water will expand and blow the walls out. 

It may need a roof, lots of paint, some new kitchens and flooring.

Obviously, some of the capital expenses like roofs, furnaces, foundation, etc. can sway things one way or the other in a large way, but how about an entire remodel for a kitchen that has bad cabinets?

JJ Mayer Is be looking at the age of the roof (hopefully replaced) and make sure it's not about to cave in.

When I replace a roof, I then take my cashflow and put it back into the reserve account until it gets back to $54K.