Make sure you are properly screening your leads the same as you would for long term renters. 

Dedicate one checking account and credit card exclusively to real estate.

If they deem your roof needs work when they evaluate it, you will have to re-roof first.If I had it to do over again with all the proper facts in front of me, I would probably have made a different decision.

This is equivalent to a free family trip to Europe if used properly.

Some buyers don't want your tenants who may or may not have been screen properly but some buyers like the attraction of having income on day one. 

I made an offer on a double, it turns out that it's on two parcels with two separate tax cards but deeded together. 

Additionally the suburbs have higher taxes compared to Chicago proper.  

As long as you're making payments on time and have proper insurance on the property, banks are happy and don't want to call a loan due. 

She played the Jesus card up big time.

I have zero stress having the systems in place with the proper people in place to manage my day to day operations.