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Im not sure if they would even sell. 

I hadn’t even thought about short term rentals for that area but that’s a really good point with the graduations.

Even if you could get $5000 per unit and every tenant was perfect, you would still lose money.

Having done the barest of research, we've looked into the idea of pooling our money to try and buy a multifamily for my wife and I, my dad, and the two friends, as the two friends also want to stop renting and to start owning, even if it is part of a multifamily/apartment building.

I just wouldn’t spend a lot of extra money providing what for me has been essentially a break even process.

That's how many months its going to take you just to break even and for it to START being a good decision to refi. 

If tenants are paying their own heat bill, they would call the gas utility and have the unit put in their own name, but tenants can't do that if the heating unit is shared by all four units.You won't have happy tenants if you are in control of the heat and you aren't even on premises. 

Is it even worth it to do an inspection without utilities on?

My guess (even though we’ve explained the process to our tenants many times) is that they assume it’s paid instantly and go about their day as normal, not being careful about the scheduled withdrawal.