The property has some exterior issues that will most likely prevent us from obtaining a traditional landlord or home owners insurance policy.

Obtain title through a mortgage or deed of trust.

Then I thought I will go for multi-family 4+ units so that I can obtain a commercial loan.

As far as the back to back closing make sure the end buyer is not obtaining traditional bank financing otherwise the deal is dead.

Well what all do you have to go through to obtain a loan with HML? 

We're wondering if we should obtain a mortgage from the outset or pay cash and then refinance.  

At this point, we did not know where we would find the rehab costs, but I explained to the seller that one of our contingencies would be a financing contingency to confirm that we would be able to obtain the appropriate financing, and he was okay with that.

GC was paid for the bulk of the work but the final draw was withheld due to problems with the new central air system (does not work now on the 2nd floor), some electrical issues with switches controlling outlets that should be independent and failure of the GC to obtain all the necessary permits from the town.   

Paul:We've never had any problems obtaining insurance coverage on any portion of our portfolio - save perhaps when we acquire a vacant building ;-)

They sent an overview of each property but what would be my first and second step into evaluating this information, then obtaining more info about each property.