It will also cover most of the closing cost if the deal falls through and I need to dump the property, preferable to a wholesaler where I can avoid real estate costs.

If they don't qualify or do not have the funds, then inform them they all have to leave.....you need to find a new tenant (especially seeing as they are already falling behind).

What happens if one of your tenants has a slip and fall, on your property, or something else happens to them?

There is a solution tailor made for you coming this fall.

Since the borrower is using the primary residence the loan will fall under those regulations.  

You need to service them spring and fall, including filling or draining the pans, cleaning the pans and vents, replacing the pads, ideally every season, and lubing the fan and the motor.

He is looking at the following locations in Massachusetts: Brockton, Fall River, Springfield and Worcester.

The city told us this falls on him as he should of known better.

I know that a duplex falls into the residential category, but I dont know if I would need a commercial loan since I want 6 of them financed together. 

Everything will make sense and fall in place for you to move forward with a decision at the point.