I've been approached by a local real estate investor to become his "private lender" on fix and flips he does. 

A home on a rented lot is harder to sell because of mortgage / borrowing restrictions (educate yourself on local lenders too).

I tried networking in a few local groups on Facebook but I don't know these people well and their recommendations have been a part of my failed search so far. 

Looking at local groups, it looks like we have one that meets very close to me in Corvallis.

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. 

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.

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

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.