Assuming you don't have a mortgage that requires a certain level of insurance, you can get a stop-loss policy covering all the properties. 

We lend up to 85% of the build costs but, generally, require that our borrowers have some experience with ground-up construction. 

Credit, jobs, income, age, married, plans for future all this matters.

I see no value in it for evaluation.Realestate.com has always been a good site for accessing properties, but they do a poor job of evaluation. 

Looking forward to the journey ahead....In my experience, very few properties in Ohio are strictly required to operate as Section 8 rentals.

typically no special license is needed when doing it for hard money loans that I am aware of. there may be states like california and nevada that are tricky where lenders need a license of some sort but for most part brokers i have seen are not licensed. 14 or 15 states require state license and NMLS registration.

With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

What special purpose equipment do you have for an ADU/Office that required unique wiring for it to function? 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Brandon Turner does a great job going over different strategies in his book "Invest in Real Estate with No (or little) Money Down".