The property has a large 2-flat main building (3 fully finished floors and partially finished attic) and a large 5 BR coach house.

If there are roof issues, trees over hanging the roof, debris in the yard or whatever client's are getting non-renewal notices.The vast majority of insurance carriers are unprofitable or have just now started to return to profitability from several bad years.

Same with the TWO roofs.

In my market, many investors aren't using agents except for commercial deals and often result to selling via flat fee broker MLS listings. 

As of now utilities (electricity, water, gas and sewage) are a flat rate of $100 per unit which is tacked onto the rent.

think about your first 1 to 2 to 5 to 10 years of ownership of a property, and the difference between:-a 1-year old furnace under warranty, and a 35 year old furnace-a house with central air, and a house without-a house with a brand new roof, and a house with a 25 year old roof-a house with a knob and tube wiring, and a fully rewired housewhich is going to have more capex? 

This may include examples such as maintaining the landscape, a minor plumbing repair, doing shingle repair on a leaky roof or painting a few rooms between tenants.

Outrageous considering we can re-roof and reside cabins by contractor without hitting a 10k deductible.

Then you can have the specialist sub pull permits for their work under their license, plumbing, electrical, roofing, etc.. 

Advantages of New ConstructionMinimal Maintenance: New construction means you won’t need to deal with a lot of the usual maintenance headaches—no leaky roofs, outdated wiring, or old plumbing to worry about.