I'm also having issue with no onsite manager, but in regards to insurance. 

I would call those contractors and ask the same thing about this property as you did those other two guys.

Shockingly he is never available to coach/ call one back after you give him money and become entrapped in his agreement.

There is no perfect software out there.

We only provide one key to the tenant and that is the key to the front door, no other doors.Some tenants will change lock on you.

Quote from @Vince Scipione: Yes, they are a popular choice where I live and work, however with the ever fluctuating cost of oil heat, many people have swapped over their boilers/furnaces to what is called a "Propane Gun" essentially it is a device that is affixed to the front of the furnace/boiler that injects the propane and ignites it.

You will learn a lot, but you just may walk away with new friends, new partners, and maybe even someone who can call a mentor.

The suburbs are each very different with some having no restrictions and some completely outlawing them.

As I see it, the only ways that real estate pays you well in the first 3-5 years is low to no leverage or a strategy that requires more work (short term rental, mid term rental, rent by the room, etc.).  

It sounds like you have an un-permitted unit, which is essentially always a risk since there has been no notice to the AHJ that it exists and they can therefore initiate a code case to have it removed in most cases.