Get a quote from a local roofer or two on what they would charge to replace the roof and run the difference between replacement costs and insurance costs.

Your local government is there to assist you on questions exactly like this one.

I'm not in your local market but if you are looking outside that and interested in the Midwest i'd be interested to share any insights I might have on the market. 

However, it's essential to consider local market dynamics.

I've been networking locally and met a successful investor who recommended section 8 to me.

I hear CDA is one of the most beautiful places in the USA, and likely going to be a great destination for years to come.Why not keep waiting, finding more creative ways to make income, and once your equity has increased even more, you can pull out some more cash from your primary and invest locally or out of state for extra cash flow. this is by no means a short term plan.

Examples - owner occupied loans for house hackers, specific market knowledge (ie - friend of mine that ice fishes and bought a short term rental cabin in an ice fishing spot that you and I would never know of), ability to do renovation on your own or cheap, contacts with local companies or organizations that would be a tenant source for mid term rentals, ways to source off market deals, etc.Whatever it is, figure that out and get started.

Do you invest locally in Ann Arbor?

I am not a local so looking for some guidance here. 

Casa de Arte is a beautifully appointed home designed and furnished by local San Miguel de Allende artists.