Good for you - careful financial analysis of each deal is critical.

If you buy now and rates have come down in 1-2 years, your property value would have also likely appreciated as values rise when rates come down in general.In regards to your point in cash flow – I agree if immediate cash flow is what you care about the most.

Then at some point in the future rent out the parents former home and purchase a "House Hack" under FHA 203b and live in it as my "primary residence" while renting out additional units. 

Investment Info:Single-family residence buy & hold investment.

@Mike Arias  When you convert your property from your personal residence to a rental property, your basis is what you paid for the property originally plus renovations you do in preparing it for rental and minus the land value.

So I have a tenant who recently moved out of my residence on good terms, actually helped me find some one to take there spot who has been a fantastic tenant so far.

According to Jamie and his team, the STR market is healthy, strong, and sustainable at this point.Jamie and his team is selling his software.Airbnb is selling their own "share in the market" but they don't care so much about host profitability in particular region as they have other region to fill the gap.Airbnb host is selling/renting their own place.That's why you get the number all over the place. 

Resident is complaining of musty smell in her apartment.

Hi,I am not a real estate investor and the extent of my real estate experience is owning my own primary residence for which I have a mortgage.  

Chicago has a TON of small multifamily available, so select your property carefully.