Just a different takeNow this is not to sayPS - those houses that were priced way too high and languish?

A few other things I'm considering;- I don't need the extra cash flow to live and am just approaching it to remove the high mortgage interest, but also hedge risk that the current stocks might tank in a few years.- Could take all current cash flow and a few thousand a year to pay off the property in 5-10 years.- Hold for a bit and 1031 into something else but am fairly confident there is not much appreciation to come on this property.

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

With a dynamic real estate market, diverse neighborhoods, and high rental demand, Chicago is a fantastic place to invest in house hacking. 

I'd highly suggest getting to some local meetup groups in MKE:  https://www.biggerpockets.com/forums/521-real-estate-events-...When you say you are considering alternative financing options, what does that mean?

For long-term growth, consider newer single-family homes in high-appreciation suburbs or well-located small multi-family properties.

I focus heavily on the sell side and on the buy side only work with high net worth individuals so the newbie wanting a 400k multifamily with an FHA loan probably isn't for me. 

He scaled with quality, going full-on luxury top-shelf.

I would highly recommend Realty One, the realtor Derek helped me solve all the major issues that came up and supported me in running the numbers for different properties.

There is always risk, and these are highly risky and regulated techniques.