I've been pretty fortunate so far in Chicago.

Coin jams are going to be your second biggest headache unless you invest in those fancy ones with tap-to-pay but those cost a pretty penny.

For the second time, I've had a guest cancel a reservation, initiating a refunding through my payment provider that brings with it significant transfer fees because Booking.com heavily promotes their "book for free, pay on arrival" policy, which is not aligned to my management platform policy.

I am familiar with Firestone park, Goodyear Heights, Fairlawn as pretty solid areas.

Here is one piece of advice When looking at areas to invest in check out this website https://www.areavibes.com/ its pretty cool it gives you a total livability score and rating for that areaBest of luck!

All of that is pretty cut and dry. 

BP Rookie podcast has a pretty good content on Airbnb, however mostly success stories.

@Makani Donaldson it all depends on your investment goals.If you buy a Class A rental, it'll usually have negative cashflow, which will be hopefully offset with appreciation and better tenants.If you buy a CLass C or D rental, it should have pretty good cashflow because you may not realize much in appreciation and you'll have a lot more problems finding good tenants.

Just take what you get for free, which is an Airbnb listing, and just put the best most spectacular pictures you possibly can on there and after you’ve done that, go back and look at your listing and try to think of ways to make those pictures even betterI think that’s pretty much the formula to success in this industry.

I mean, you don't need to clean the property or pay local taxes since there is no use so I think this is pretty fair.