I would remind them that the house is in the condition in which they rented it and they accepted it as is.

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Given statement of condition, I would think value-add is the opportunity at hand.

However, Allstate is capping their landlord insurance at $750,000, which creates a coverage gap I need to address.I’m looking for options to add at least an additional $750,000 in coverage and am wondering if anyone has experience with Difference in Conditions (DIC) coverage or Excess and Surplus policies.

We also have a "Pace Report" (PR), which tells us where we are at in revenues for various months, as compared to where we were exactly a year ago on this date.  

Exactly.

As mentioned above look in the loan docs for reference to 'condition' or 'use'. 

A good broker should be able to tell you a range of rates given specific criteria if you can tell them what kind of deals you are exactly looking at (ex. in central Boston, 10-20 unit, 90%+ occupancy, 30% down).

However, with the rates and conditions of any triplexes and fourplexes we could find (we did find one, but it's in the Pendleton Heights suburb of KCMO, so we were worried about it being too dangerous of an area), we were wondering if it's worth it to buy a duplex and rent out the other half to help pay the mortgage, or if it's more worthwhile to rent an apartment and try to save up to buy a residential or commercial MFH later?

They will tell you exactly what is needed, so there's no confusion.