In my area these are rare so they are difficult to set market rent, and I imagine get a lot of wear and tear with a lot of occupants living there. 

I bought a single family because I thought I could house hack in the same way as a duplex and in ways it certainly could have and did work but I didn't expect the relational aspects of having people living in a property I purchased.

I live in Portland  Maine , I am new to real estate investing and looking to connect with any local investor.. thank you.

. --- They will offer to fix them in exchange for lower rent, but ask yourself, if the tenant has been living there for 25 years, why isn't everything fixed already?

I live in the Newark area.

Do these folks have temporary  overage for places to live?

I lived there for a couple years and I met this guy who has bought and managed a ton of property there. 

When your tenant stops paying and communicating, who will knock on the door to see if they still live there?

A good way into it may be doing a house hack or live and flip then pulling the equity out in a refinance.Tons of ways to make money in this game!

Now the living room and 2 bedrooms that just had new flooring put in them 8 months ago are ruined from the leaking water from the HVAC and have to be replaced again.