Like you said, you have to make deals and look outside of the typical markets. 

Most out-of-state syndications or hedge funds wouldn’t typically consider the cities you mentioned.

Maybe selling is an idea worth considering if the house is a Mona Lisa and kind of beyond the general reality of typical tenant's maintenance obligation and ability, and they aren't paying for the additional quality.If you really want to keep the home, you may find a way to be very happy about it with the right team, whether it be property management, electricians, contractors, or tenants.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, immediate cashflow and at the lower end of relative rent & value appreciation.

Make sure everyone knows a cleaning schedule, expectation for common areas, how are you splitting utilities, guest policy, etc. 

If you see utilities increasing, is there a way that you can push this on to the tenant?

In any contract you don't typically need a clause saying what you CAN do, its assumed you can do anything legally allowed as an owner including sell.

From what I've seen, typically two people doing a flip like this have different skillset so one person is doing different things than the other.

These are what we call "A-class" markets—areas with strong fundamentals, high demand, and typically excellent long-term appreciation.

One of the biggest challenges of investing in Rustbelt cities is knowing where to invest and properly understanding the cooresponding pros & cons.Here's copy & paste advice we share to help to address this challenge:-------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?