1st Out of State Rental Property (or AirBnB)?

[Casandra M.]

We currently invest in rental properties in our home state of Wisconsin but are looking into possibly purchasing a 1-bedroom or studio condo in Lincoln Park in Chicago, right near the zoo (with a great zoo view and bit of a lake view), with the intent of trying out AirBnB and other short term rental sites for the first 6 months-year of owning the property due to it's location. We are a bit nervous jumping state lines, even if it's less than 2 hours away.

What has been everyone's experience in purchasing an investment property out of state, near high-tourist areas?