@Gene PanicciaManagement fees vary, but it's not uncommon for a PM to charge fees for managing tenant-paid utilities or coordinating repairs.

At the end of the day, both of these respective vendors/individuals are paid when the deal closes. 

I suspect this is what you paid $1600 for, Alicia.

The IRS views this as a related-party transaction, and deductions like rent paid to yourself wouldn’t qualify.

They sell you a package to enter and then find you people to stay and never paid you back!

Those failures are  more negligent than a PM allowing a guest who paid with expectation to stay at the house to remain there in the middle of winter when they arrived on a Friday evening as you described.For now you will have to rely upon insurance, I don't believe the PM acted unreasonably given the circumstances.

- Usually a 5 unit with a boiler means that all the units share the boiler heating system.Which specific utilities in which units are paid by tenants vs shared?

I was going to bring up that the seller financing doesn’t matter if you plan to get a construction loan as the seller financing will have to be paid off. 

Was paid sales commission to sell it to myself.

That loan is being paid off by someone who checks the box on the conventional loan application that they will be occupying the property.