I am closing soon on a new house and will be turning my current house into a rental. New property is a multifamily and I will be renting out half and living in the other half. So two properties I will be managing myself. Get in here and tell me your worst stories, biggest regrets, how big of an idiot I am, etc.
My wife and I rent out two properties in Chicago (one of which we've been renting out for awhile and have gone through a number of different tenants). You'll either want to have someone on tap up front that can take care of regular repairs (painting, basic electric, etc.) if you can't do that yourself.
Get a basic understanding up front on landlord/tenant law where you're at. Don't want a foot fault on things like requirements for how you need to rent it out, who you have to rent to depending on if they meet the right conditions, etc.
Make sure you have something in the lease that puts basic house maintenance on the tenants AND specify those expectations up front. If someone doesn't know how to light a pilot light for example, you want that responsibility on them.