Can I encourage the seller to file a claim against their homeowners insurance for some of the repairs?

I would encourage him to get his license; it will prove very useful if you continue in this business.  

I would encourage you to gather the info on what your actual cash flow (positive or negative) would be.

Even without the BRRRR strategy, this is a very powerful way to take advantage of time (do it a few times for a few years while young) and subsidies that encourage owner-occupants by giving them cheaper mortgages. 

If it's the latter, I strongly suggest you join a team that will encourage your entrepreneurial spirit and investor pursuits.

I also encourage you to network face to face at a local Real Estate Investment Club.  

Many companies who build equipment have to prove they are ISO 9001 compliant to sell to some of their customers.

I realize my properties are not  really what the typical customer wants.

@Jay Hinrichs, that's encouraging to hear!

Their fees are very reasonable and so far their customer service has been great.