It is also for that very reason that you should be wary about going in as I do feel that the Pittsburgh has gone pretty high up in it's property values. 

Pairing that with relationship-building will help you uncover off-market opportunities and find local experts who can guide you.For meetups, here are a few ideas:Indianapolis Real Estate Investors Association (Indy REIA): They have a mix of virtual and in-person events and are a good starting point for networking with other investors in the Indy market.Louisville Real Estate Investors Group (REIG): A similar organization for the Louisville market, with educational and networking opportunities.Check out BiggerPockets Meetups: Many cities have local meetups organized by investors active on BiggerPockets, and they often include virtual options.Facebook Groups: Look for local investing groups like "Indianapolis Real Estate Investors" or "Louisville REI."

I think you forgot to include the question.

Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

Also, SAAS platforms are supposed to include support and service (that's the last S), but the quality varies greatly from company to company. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases.

The deal sounded good at the beginning but thought it included his fee and it didn't so he's tacking on his 20% on every bill. 

How much do you net (including financing costs)?

In total, including money lost from rent, legal fees, and repairs, the situation cost almost $30k.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases: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, 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, high cashflow and at the lower end of relative rent & value appreciation.