Keep in mind that the economy is great right now, but when the economy turns, questionable neighborhoods get even worse.I feel your pain.

Hi everyone, this is my very first post and I need some advice.Background, I leased a house in CA to a pain in the neck family for 1 year.

You need to consider how much pain your each willing to take and for how long. 

If it is, technically I can terminate their lease and get rid of a huge pain in the you know what.

It's a huge pain in the butt and rarely worth it. 

There are a lot of things to like about Chicago as a whole, but many investors that I know have experienced some pains with single family flips in recent months. 

I worked 3 jobs to fund deals, and I loved it because I earned it after going through the pain.

I'm looking around and still trying to find a multi family property that my family can owner occupy. it's all very exciting and nerve racking at the same time.Best of luck to you on this property and to the next one.I financed this through a conventional loan which can be painful since it requires 25% down when it’s not your primary residence.  

Most of them are unreliable, not very skilled or just a pain in the butt to deal with. 

I could afford to replace the whole cost but it would be painful so does that mean I should get insurance?