Seems like such a gamble to me but I really love the place.

Owner-occupied ratio no longer met, HOA being sued etc.So in essence it's a gamble anyway when hoping for a future sale process being smooth when talking about Condos.

As far as my goal goes, I want to buy and hold in this specific market as a live-in college rental, 2nd exit strategy airbnb for the nearby sports arena. 3rd sell it off because its a nice area w/ schools. 

I live and will invest (at least to start) in Kansas City and the surrounding areas.Let me tell you a little more about myself:I enjoy traveling, watching sports, reading, going on early morning runs, eating healthy and (most importantly) spending time with my family and friends.I'm a big math nerd.

I love sports, namely basketball "GO HEAT!"

BTW I spent about 7 years working in Black Hawk and never lost at gambling.

I think @Brad Larsen also gave you some great advice about the benefits of a career in Property Management as well as advice on taking a gamble on yourself, the way he did. 

I am a huge New England sports fan, music lover/musician as well as a sport car enthusiast.  

Since it seems like you need more money and less debt, I think the best way you can get to the "real estate gambling table" is to first get more money.  

What you are doing is gambling with your future.