No, they probably won't cash flow in a traditional sense right away, but you'll put much more money in your pocket using tax mitigation strategies that you'd ever get from cash flow on SFH in the midwest. 

Cash out Refi)Pros:- Typically lower interest rates than the other two optionsCons:- Higher closing costs- You lose your current interest rate that is probably significantly lower than current ratesHELOC)Pros: - Lower closing costs- Interest only for what you use- You can choose to use it or not depending on your future plansCons:- It is a second lien, so they typically have higher interest rates- Sometimes it is a variable ratePrivate Lender)Pros:- Less government restrictions that you need to follow- HUGE amount of flexibility because everything on it is negotiable from interest rates, to payment options- Not required to leave 20-30% of equity in the property, and no PMI if you have less than 20% equity- Closing costs are minimal.

I think @Paul Sandhu captured the list of skills you need to find, and that you can probably find someone with "3M Talent" (or at least "2M Talent" to cover several areas.)

Tenant Default: 0-5% probability of eviction or early lease termination.Section 8: Class A rents are too high and won’t be approved.Vacancies: 5-10%, depending on market conditions.Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Class B Properties:Tenant Pool: Majority of FICO scores 620-680, some blemishes, no convictions/evictions in last 5 years.Tenant Default: 5-10% probability of eviction or early lease termination.Vacancies: 10-15%, depending on market conditions.Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, balanced amounts of relative rent & value appreciation.Section 8: Class B rents are usually too high for the Section 8 program.Class C Properties:Tenant Pool: Majority of FICO scores 560-620, many blemishes, but should have no convictions/evictions in last 3 years.

Will Griffin, Jr. at Griffin Clift Everton and Maschmeyer is probably the best investor-oriented attorney in town.

Midwest is stable and doesn't have wild fluctuations like California, probably didn't go down 50% in 2008.  

If it costs $150,000 and the ADU rents for $750, then it's probably not worth it.Here's a guide on how to analyze a property.

Market rent for similar units is probably closer to $2,300–$2,500.Older building with deferred maintenance – needs work, but nothing major that can’t be done over time.Units are outdated – probably last remodeled in the 1980s or 1990s.

Tenant Default: 0-5% probability of eviction or early lease termination.Section 8: Class A rents are too high and won’t be approved.Vacancies: 5-10%, depending on market conditions.Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Class B Properties:Tenant Pool: Majority of FICO scores 620-680, some blemishes, no convictions/evictions in last 5 years.Tenant Default: 5-10% probability of eviction or early lease termination.Vacancies: 10-15%, depending on market conditions.Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, balanced amounts of relative rent & value appreciation.Section 8: Class B rents are usually too high for the Section 8 program.Class C Properties:Tenant Pool: Majority of FICO scores 560-620, many blemishes, but should have no convictions/evictions in last 3 years.

If you are doing unpermitted work, it’s either too small a project or you probably don’t want to spend the money.So the market for such inspectors is probably small.