I would designing, renovating and managing the property.

The #1 reason that Landlords fail, according to the American Apartment Owners' Association, is the landlord's failure to manage to the lease.  

I’d love to hear your insights or experiences managing properties with similar setups in Pittsburgh.

I'm a broker and property manager.

Do you recommend making relationship with property management companies?

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.

I'm a investor, flipper and property management company owner who specializes in central CT.  

Property Manager – This is another one I really need help from the bigger pockets community in the local area.

So, I’m curious how you are managing to find your deals, whether you are buying at auctions or via marketing direct to sellers.

I'd start by talking to others who are landlords or property managers in your area.