I will have a down payment but with the income my other rentals will make in the next year after reserves taken out, will cover the downpayment for the loan.

If they pay after that, you use the late fee to cover notice service Marshall fee.Train them early and often!

The money received from the auction will need to cover the legal fees for the auction, the original loan.

As a former VA employee and a mother of a son who is a Navy veteran taking advantage of the post 911 GI bill for schooling, I have to say at least some of what your tenant is claiming in terms of not being able to pay the rent sounds like what comes out of the south end of a horse going north.Depending on what your rent is, the BAH from his GI bill should, alone, cover the rent. 

We initially signed a contract for asking price on the property and I subsequently asked for $20k break on the price based on the inspection results, which I thought was a fair ask and the seller signed the addendum accordingly.Now the seller is asking me for another $6k to cover costs of heating unit replacements (after further inspections done by the seller as required by the city) since the units are over 50 years old and cannot be brought up to city inspection requirements.

We initially signed a contract for asking price on the property and I subsequently asked for $20k break on the price based on the inspection results, which I thought was a fair ask and the seller signed the addendum accordingly.Now the seller is asking me for another $6k to cover costs of heating unit replacements (after further inspections done by the seller as required by the city) since the units are over 50 years old and cannot be brought up to city inspection requirements.

In your scenario you will likely be using the security deposit to cover rent, but that should be spelled out in your itemized list that you provide.

The tenants rental property will cover all of their personal belongings and since you are using a PM company I would assume you will not be keeping any landscaping equipment, tools or possessions at the premises to need that much coverage.

I have carefully gone through the documents Lease Runner has created for Massachusetts and been very impressed with their ability to cover the Massachusetts laws in detail.

How do I get the rest of the 90% covered?