Goal is buy and hold. something that will supplement me in retirement/keep me busy when I retire at 49.

Supplementing with some short term income is a good way to make those payments.    

My long term goal is to supplement my teacher's salary with passive income to the point that my sweet wife doesn't have to work anymore.

It's also more cash than I have available so I would have to supplement with a HELOC or refinance.

Have to admit some of the investing terms get overwhelming, but supplementing the reading with youtube videos of "what is ROI?" 

Our plan, and strategy, is to begin our REI portfolio now (or very soon), so that in 10 years we use REI to supplement my retirement pension and in theory, be financially free.Like I mentioned to @Eric Jones, OOS investing in a more passive manner makes the most sense for us now.

You can use cash generated from the losses if any to supplement your 1031 purchase.  

My older brother, who is currently flipping his first home in Philadelphia, enlightened me on the possibility of real estate as not only a supplemental income but more so a way out of my house via house hacking.  

Unless Chicago experiences similar appreciation as LA, which I don't see based on pre-recession vs. post-recession median home sales price numbers, the implementation of a Rent Stabilization Ordinance will discourage investment from buy-and-hold investors, who will start to see a squeeze on cashflow (restricted rents w/rising property taxes) supplemented by sub-par appreciation gains.

I have recently decided that I must supplement my current government income through passive means so that I can set myself up for a great position to "escape the rat race" when I transition to civilian life in a few years.