I am particularly interested in turnkey properties and single-family rentals, but I am also open to exploring other options, including duplexes and different investment strategies. 

@Chelsea DiLuzio the Midwest markets are way different than the markets out west!

@Derek SoohooIf you're looking to invest in multifamily properties in Chicago, start by researching different neighborhoods to understand rental demand, property values, and landlord regulations.

The only difference is one is priced on daily basis and one is not.

Obviously, if there is a large hole in the wall or they painted a different color, then you can charge them to paint.

I am baffled why others try to argue it's different, maybe we just value our time and skill differently than they there's.

Edit: For SFH A simple answer: everything is negotiable and every agent runs their business differently.

I am looking forward to meeting people from different aspects of the Real Estate Investing world.

If I am putting that money to work with investments and not spending it what’s the difference if I use it for real estate to fuel my retirement or my 401K.

A typical policy for short term rentals is going to cover most, if not all, of the perils you have listed.But if it is a homeowner's policy or standard landlord policy, the insurer may well deny claims, since the property is being used differently than what is described in the policy.