Hey Everybody! 

Brief intro: while I was in the Marine Corps, I found BP and started absorbing as much info as possible. I studied hard for a couple years and when I changed stations, I fell off the bandwagon. Recently I found a property that I thought was extremely intriguing, which led to me running numbers and trying to make a determination if this property was the right fit for me or not. (this property is now off market) This sparked that REI motivation and mindset that I discovered a few years back. I'm back into the baby steps of studying and game planning, but I've done some research and am considering pulling the trigger on my first investment property. My only RE experience up to this point is purchasing a SFH with the VA home loan. Owner occupancy requirements for this loan is (Typically) 12 months, which I am fast approaching. My idea is that, I will find another property (Single family or Multifamily) ; buy it using the remaining entitlement from my VA loan (zero $ down) and live in it while I rent out my original SFH. I have talked to both the VA eligibility department and my lender, and this is a legal and doable plan. I am bringing this here, so I can hopefully get input, suggestions, or recommendations on things that I may not be thinking about or considering. As stated this would be my first investment property so there are nerves involved and uncertainties so take it easy on me! I'm in the process of finding local meetups, along with continuing real estate education online. A couple questions and thoughts that have came across my mind are below.

Contributing factors: (My goal as most newer investors is to reach financial freedom)

-Area: Western Suburbs of Chicago.  

-Monthly Payment: $1,189; Average Comparable rent in general area: $1,400-$1,800? (That I have found)

-I will only physically be in this area for another year and a half. (Worth the hassle? Could look into property management after I leave? Could liquidate both properties and use towards another adventure? 1031 Exchange?

-I considered opening up an LLC and transferring the title for my current SFH into it prior to renting it out; but after speaking to my lender it's thought that there is no real financial benefit with doing this, and I personally would still fall liable for the mortgage, as well as legally liable. -(Pro's/cons? Will I lose out on some of the tax benefits? Should I consider, refinancing under an LLC with a FHA loan? why?

Should I readjust my mindset with this plan? if so Why/How?

Are there any thoughts/suggestions that come to mind when reading?

If the plan is dumb feel free to tell me, it won't hurt my feelings it will just help me while in pursuit of my goals.

***Thanks for any provided input. I appreciate it!