Hopefully, my insurance will pay to replace the roof for House A, but I am debating whether to replace or repair the roof for House B.

I just started working with THD, I had the same situation as Shankar RamaniI had a 3/2 SFH posted for LTR, they reached out asking if I am open to short term rental, I was hesitant first but after searching the company and their business model, I was willing to take the risk if they pay me a good premiumThe person who reached out to me works with the insurance side of THD ( they have corporate leasing department too), and her tenant had a fire damage in their house so the insurance company wanted the tenant to stay somewhere until the house repair is done.

Or if my landlord homeowners insurance policy will cover this?

All three generate leads from insurance claim residents and traveling professionals (medical and the trades).One of the advantages of FF has been that it's forced us to have systems in place to create leases, accept security deposits without co-mingling and provide "live" customer service. 

If it's not included in the rent, many companies charge a flat fee to monitor & pay utilities.2) Assuming you're referring to resident benefit packages, renters insurance, and other charges for services the PMC offers to tenants. 

For example, I work with insurance relocation companies to house their clients who lost their house.

Specifically in SC, though, I would check two things - 1) see if the ATI exemption applies and actually quote the taxes for that particular property on the county tax estimator tool, and 2) get a ballpark quote from your insurance partner on the particular property.

We're flipping these properties to investors and or first time homeowners.

Be aware of insurance rates, they are higher than most other states.

Is there a type of mortgage insurance or bond you can get for owner financing that secures his position?