I am considering the pros/cons of doing this without a property manager or real estate agent. 

I occasionally get requests to manage commercial and love to have a referral source. 

Cleveland is a great market if you know how to navigate it and have a good property manager.

Consider managing remotely you'll have to be willing to travel 3 hours when needed or find a way to handle it virtually.

I would focus on a strategy and you and your brother like (Do you want day to day management of a house flip?

@Tyler DavisUsing Locations in QuickBooks can get tricky, especially when managing multiple properties.

I am a voice of common sense and help them come up with the best way to manage STRs.

Quote from @Obed Calixte: There are a ton of free tenant applications online and through property management software companies such as turbotenant, rentspree, zillow etc.You will want your application to meet any state specific guidelines (if applicable). 

Are there property managers who specialize in managing housing for section 8 tenants?

Not surprised he is a property manager.