I am currently helping my wife with our newborn third son, so will reach out in the coming days/weeks as time permits.Looking forward to connecting and learning from you all and working with you as well!

Third issue. 

Far better performance and eventual resale.

Also, you would not know the quality of work the contractor performed ten (10) years ago.  

My preference is two so I can test two brokers and from then work with the one that performs.

@Edgar Joshua Find a third party intermediary to service the debt...if that's not an option look to ACH.

Before I spend a lot of time and effort performing more due diligence on this property, has anyone else dealt with a flat roof before?

If the lender doesn't perform in a timely manner, the buyer forfeits the escrow.The lender has been slow to respond on a few occassions but nothing like the week and a half it took for the seller to schedule the appriasal inspection... stating that the tenants needed to have proper notification.

I have personally dealt with this thought as I have a duplex and the third floor is an attic space that would rent for $8000/month.

When a party related to the transaction has more than one role in the transaction or is employed by or has an ownership interest in a company that is involved in the transaction (including but not limited to third parties such as marketing companies, builder / developer, broker, or realtor), there is a non-arm's length or at-interest risk.