He had insurance on the S-Corp for one million and none for himself.

Not if insurance paid for it.

Sometimes they forget to tell you that many tenants in Detroit don't pay (depending on the property manager skill and the type of tenant) - but taxes are very high in the city and so is insurance. 

The triplex is much more popular with traveling work crews for specialists in the trades and insurance relocations, so if we were to do it again, I would probably worry less about making each room it's own rentable space and save a little bit of those costs. 

More insurance will cancel short term rentals.

You might try corporate housing by owner, or try getting in contact with some insurance companies for replacement housing, or traveling work-crews, etc. 

For structuring your business, consider whether you actually need an LLC or if umbrella insurance might be a simpler alternative.

He isn't a motivated seller.If it will rent for $1900  a month, that means to make money you have to have a payment that includes, principal, interest, prop taxes, insurance, at less than $1400 a month. $190,000 at 3% interest is P&I $801 + prop tax plus insurance a month.

We are now appealing a denied claim with the insurance company.

Another idea that we have been exploring is using the cash value of whole life insurance funds for emergencies.