I'd sell the property and 1031 in to something without an HOA. 

Hi Michael, I'd be glad to help answer some questions for you and/or locate a duplex that would work well for your goals.Feel free to connect!

Chicago has a fantastic real estate community, and there are plenty of networking opportunities.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

Hoping that each of them produce $1500 in rent, I’d like to get $3,000 total which would be enough to cover my mortgage. 

If my main goal was cash flow, I'd sell all my properties, except one and put the money into index funds/stocks - cash flow has been great the past 3 years.

I'd call that transparency. 

I’d recommend connecting with local property managers and agents as soon as possible—agents can help you identify deals that fit your BRRRR criteria, and property managers can give insight into rental demand and market rents.

However, there are still plenty of tax benefits when it comes the income you generate from your multi-family property that you can deduct from. 

I'd appreciate the same if anyone needs assistance in PA (primarily counties of Lancaster, York, Lower Dauphin, Cumberland, Adams, Lebanon and Chester).