I got the inspection done, and he was very doomy gloomy about damages and issues he found. 

What do you do when your tenant doesn't pay rent and your water heater goes?

You the landlord is only responsible for providing a safe and comfortable living environment, clean water and heat to your tenant.  

Are there any major repairs coming up (ie how old is the roof, furnace, hot water tank, etc)?

Trouble will come in the form of units that are tougher to rent because they are difficult to get in and out of, as well as more damage from drivers that lack the skill to maneuver into the units in BOTH buildings

Closing on a building that allows the tenants to have their own washer and dryer but the water bill will be mine.

Sewer, water and electric are at the street.

If the pointing isn't well maintained, it can be a superhighway for mice and water intrusion.Knob & tube wiring. 

I imagine that's due to roof damage and leakage. 

The savvy investor of 2019 will be maneuvering daily through waters that are by no means treacherous but will require a close-up look and heavy scrutiny of any risk they take.