The back house had long term tenants and the place looked dirty - wasn’t taken care of or cleaned in a very long time.

I argued we were already done and the contractor had been paid and they relented.But, yes, if you have an insurance claim on a mortgaged property it is reasonable to expect the lender will want you to give them the money and they will pay the contractors.Sounds like you did not carefully read all the paperwork at closing. 

No one cares about your property, your rehab, or your finances as much as you do.

The city dose take care of the water, sewer, and streets. 

They don't really care about ROI .

Hey y’all, I have just signed into a contract with my first rental management company to take care of my duplex while I’m deployed.

Granted this often covers roof repairs, exterior insurance, lawn care, sewer and some other expenses.

How is responsible for lawn care?

Be careful here!

He also recommends bringing in specialists if he sees something that may be a concern but is outside his area of expertise.I do not know your level of experience but often when you read a home inspection report they make the property sound like the place is a piece of s**t but most of the items a decent handyman can take care of in a couple of days for a few hundred dollars.