The property is in overall good condition but may need a roof ( around 10 K ) within 2-3 years.

Defects-Deferred maintance (roof leaks, windows rotting out, mechanicals not workings) must be considered. 

I thought I had a leak but have had the whole system looked at and nothing was found.

He then let me know that no obvious sources of a leak are known of in the home and no evidence of leaking is happening, but the high water bill is an indicator of a leak somewhere.This brought up a fundamental question that I wanted to put out to you and learn from you on:  if the tenant pays the water bill (it is in their name with the city) and there is  SUSPICION of a leak, who's responsibility is it confirm (and pay the fees that would be associated with confirming and/or finding the leak)?

I purchased a serious value add 12 unit apartment building in Indianapolis in April of 19' and spent the last 9 months completely turning it around:- Over $150k in renovations: new roof, completely updated common area, most units renovated and turned, new furnaces, plumbing and electricity updates.- Went from 9/12 units occupied, mom and pop managed and  all well under market rents and most not paying on time.

The tub has a small leak, but I believe the leak is from the metal drain that has deteriorated and there's a piece of it missing that forms the seal.

New windows, roof and update internal.

However, the repairs minor ones such as leaks have cost me money.

We Still had a roof over our heads and it was a flip in the making, in my eyes a win win situation.

We added roof, central HVAC, and some structural repairs.