This isn't always the case, but in general, I've found Section 8 homes tend to require more frequent minor repairs.

This being said, I don't believe we'll be able to meet the income requirements to qualify for a conventional.This leads me to believe hard money or private lender is more the only option to get my foot in the door, use my business to make repairs at very good rates, build some equity then refi once the balloon is due. 

In this manual (which I assume could be modified to provide to tenants) I include all the financing information (which you would not include for tenants) bank accounts, mortgage accounts, payment information, and mortgage payoff), a list of the contractors, what each contractor does, a list of upcoming planned or necessary repairs, and a copy of all leases associated with the property.

Normal repairs are absolutely NOT covered by insurance.

Hard Money will usually finance 90% of your purchase price and 100% of your repair cost up to 70 or 75% ARV (after repair value).

I'd call insurance before having any sort of plumber to come do any repairs.

I thought I could solve the vagrant problem by buying and repairing the buildings.

I would say that the value he brings is finding the deals, doing an initial diligence, having a local team set up for renovations/repairs/property management as well as knowledge of the neighborhood.

The second property will need 25k in repairs, and rent for 1350-1450 monthly.1.

Quote from @Dan Grove: Some combination of cash to seller, closing costs, repairs, construction, paying off arrears, assignment fees, commissions.