Considering the high deductible on House B, I am only filing a claim for House A, and coming out of pocket for the cost of repairing or replacing the roof for House B. 

Whereas habitability issues, like structural repairs, may.

If I don't make the repairs to the MH I won't be able to rent it at all.

you mention ARV - what is the cost to repair the property to get it to that ARV?

The 70% rule suggests buying a property for 70% of its ARV minus repair costs to ensure profit.

By the way, the tenant should be charged for this as part of "cleaning and repairs." 

Maximizing Deductions: You can still claim tax deductions (mileage, repairs, management time, etc.) on both properties as long as they’re legitimately related to rental activity, even if one isn’t in an LLC.

That does not qualify as "managing repairs."

think about it:-when you buy a property, you'll have a down payment, closing costs, rent-ready costs, costs to get set up with a PM, a commission to place a tenant... maybe some light repairs after the tenant moves in...

For a beginner, it will be wise to start with a property that requires less hands-on management, like a turnkey property or one needing only minor repairs.