I just need to learn to embrace the idea that spending money on an investment property, and carrying debt that makes me money, is entirely different than financing a new sports car, or putting a vacation on a credit card.  

Stop hanging out with your deadbeat buddies that spend all day drinking, talking sports, and otherwise wasting away.

Of course if I was able to time those peaks and valleys I'd be sipping mai tais while watching obscure sports on TV and not pretending to work at my desk.  

I had a sales rep agency in the sporting goods business.

It might not be a productive use of my time but it will be more entertaining than listening to the same old boring news and/or sports radio.

Reffing High school/ youth sports

Not that Indiana isn't a great place but I'd rather be where the action is and enjoy summer sports all winter long in the sunshine and warmth. 

Cleveland is often known for its famous sports teams and continues to develop the riverfront area between the stadiums.Cleveland’s job market continues to grow with a sizable push from the health care industry as well as large companies such as Cliffs Natural Resources, Forest City Enterprises, Sherwin-Williams, KeyCorp, and NACCO Industries.

I personally love living in a big urban area and enjoying all of the attributes of it(walkability, mass transit, culture, diversity, incredible restaurant and nightlife options, architecture, pro sports, entertainment), but I realize that's not for everyone.  

Yes, you can buy units in Memphis for $5k per door and I know how tempting that looks for a California investor, but it's a contact sport and you need to be physically present to do a project like this.