Chicago area short term rental investment

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I have been searching for a 2 bedroom property on the northside of Chicago (Lincoln Park, Roscoe Village, Wicker Park, Bucktown, Lakeview, etc.) for a family member to occupy 1-2 months out of the year so that they can spend an extended period of time each year with my children. My hope is to rent out the property the remaining part of the year and turn this into my first REI property. The challenge has been with high HOA fees and taxes, as well as association bylaws related to short term rentals, even at best the cash flow each year would be minimal. With minimal cashflow I'm leaning towards just finding a short term rental for this person each year.

Is there anything I might be overlooking in a unique situation like this or suggestions anyone might be able to offer?  Thank you in advance.

Matt