Please keep in mind that many entrepreneurs and investors leverage stable, well-paying W-2 jobs while growing their portfolios and businesses (read the excellent Phil Knight autobiography Shoe Dog for a great example of this.)  

If I was in your shoes I would look for something that needs a lot of cosmetic work.

@Travis Bodnar,  your post has me smiling because I was in your shoes back in the day.... 

If I were in your shoes, and I have been!

@Andrew AcunaPlenty of arm chair investors that don't know the difference between a shoe horn and shoe molding.Regrettably the majority of tenant problems are created by incompetent landlords.You have read the posts....my tenant regularly pays late.

@Jessie Nunley"Don't take advice from anyone you wouldn't trade shoes with"Don't worry about them, you will get A LOT of negative feedback, being scared about the "what if" scenarios, whereas if you have a business plan-- trust it and move forward!  

Heaven help the rust belt when the shoe falls. 

I buy Nikes running shoes, at the outlet mall.

And while designer accessories can have resale value, I've obviously been unable to re-coup some of those dollars through eBay sales...Some lottery players wouldn't dream of spending so much on a pair of shoes... unless they won the lottery, of course.....

That's what I'd focus on in your shoes.