I'd be willing to consider coverage for the improvements as they exist and not necessarily the replacement costs. 

If the PM  has to ask the owner fore permission for an expense every time, it can delay the repair, irritate the tenant, and make it difficult for the PM to retain tenants and uphold a certain standard of service.  

I won't say they don't exist, because I know several that are appropriately licensed and can make these loans, but they tend to specialize in lending to well-qualified borrowers that the banks won't touch.

As the new owner, you would need to operate according to the terms of the existing rental agreement (written or verbal) until you enter into a new rental agreement with the tenant.In the absence of a written rental agreement, you will need to proceed with caution.

Again this is not a town where property management companies exist. 

But I have pre-existing commercial relationships with those banks.

I don't know if there is a way to take over the existing hard money loan.

However, underwriters don't want to do it any more because of the exposure referenced above.Ways still exist to do it, but the explanation is too long to discuss here. 

The stair faces the yard, and it's not within 6' of an adjacent property.I found the code section.CHICAGO CODES 13-200-260 Porches and Decks Existing porches and decks may be repaired or replaced in the same location with construction of the same type as that of the existing porch or deck. (1) Existing porches not exceeding three stories in height may be extended up one story to the roof level regardless of their location with respect to the lot line or other buildings on the same lot, if in conformance with the Zoning Ordinance. (2) Existing porches may be enclosed, regardless of their location with respect to the lot line or other buildings on the same lot, if construction requirements of Chapter 13-60 are met.

Is $3750 ($250/hr x 15 hours) a reasonable retainer fee  for an eviction of a buyer on a seller financed transaction where buyer is overdue on balloon payment (by 13 months), but continued to pay monthly payments, although most were late and no late fees ever paid in 6 years.