I own a rental property in Chicago that currently has a lease and the monthly rent covers the mortgage and HOA assessments exactly. 

This area is just going through the roof.

You need to look at it like the business it is and maximize your profits.You mentioned at the end wanting to, “at least get the tenant to cover half your house payments.”

I rent out the spare bedrooms, which covers the mortgage, taxes, insurance, and repair reserve.

If the property has any issues that would cause someone to not be able to live there (roof, plumbing, broken windows, holes in the walls, etc.) those items would come back subject to repair on an appraisal and need to be fixed before you can get any type of mortgage financing.

@Benny Gelbendorf The roof and gutters would be around $1000 (fix top few rows of brick on chimney, replace pipe boots, split boot on electric meter mast, new gutters & downs, maybe gutter guards on some areas)The mold I do not know, I would imagine in the $1000 range, but would need an inspection from a mold expert.I am an exterior contractor and my partner is a handyman/general contractor.

He may already be 10-15 years into a 25 year roof so you have to calculate based on remaining life.

If you are relying on credit cards and anything goes wrong which is likely on a first deal, you will be stuck without reserves to cover expenses.

There is a ton of info here covering ever conceivable question on it.  

My little brother was stabbed 4 times with me trying to put his ear back together as it was split in half and the bottom half of his ear flopping down the side of neck macking sure hes ok, trying to help my buddys from being stabbed themselves with no success findind out when the ambulance got there that my brother was on the brink of death by blood loss and friend being slashed but not being able to feel it because of the adrenaline or see it because his clothes were covering his cut while shaking off the brass knuckle hits to the back of my head, i was shook.