Also, I would consider trying to BRRR some single family homes if I found the right deals. 

With Chicago minimum wage @ $12/hr, assuming 2 working adults (working minimum wage), household income would be almost 5x the monthly rent for my 2BR apartments, leaving about $3k/mo for other expenses.

This is sort of a rough draft of my plans, I would either like to get a multi-family (nothing bigger than a quadplex) or single family 3beds at least and house hack them for cash flow. 

Hi,I'm a new investor looking for single family homes to buy and hold or possibly flip.

The rent price is tough for a single person to afford, and a couple living there would have a tough parking situation. 

Every single state in the US has a LLC Liability shield in it.

It is a single family home on a property that is zoned commercial.

If this is a large condo complex you could do it as 5 vanilla Fannie 30yf loans; if this is a smaller complex or you prefer a single blanket loan, it'll  be a commercial financing scenario... adjustable, 20-25 year term, etc.

Our plans: buy and hold single family, duplex, triplex and fourplex properties for long term rental income.

The house was originally a duplex, but the city enforces a rule that a duplex that sits vacant for 12+ months in our zoning district, then it will be a non-conforming use and thus must be converted to single-family.