Would my first step be to identify market (Cleveland) find a property then before closing enlist a property manager?

However, I am also on track to commission upon graduation in the United States Air Force (prior enlisted 6-7 yrs).

Here's my thought process in (a condensed version of) pros and cons.Pros:-I have an agent I trust, with whom I served with at the end of my enlistment.

One option is to enlist the help of some friends/family and buy them lunch in return.

I have about 5 years left in my current military contract therefore my goal is to walk away from the Air Force at the end of my current enlistment to continue grow and scale my business. 

Buying now forces you to either liquidate, be an out of state investor, or move back to this area.If you keep your head down, work hard, save, continue to learn and avoid the pitfalls that A LOT of junior enlisted make (expensive cars, rushed marriages, etc), you'll be set up perfectly for when you decide to get out.

I was shocked, it was hard for a while, about a year really, and I enlisted in the military before finding out she was making a trail but reported for basic training etc after I found out she was leaving.

Keep calling, or enlist your tenant's help in talking to/inquiring with other residents. 

My time was MUCH better spent elsewhere…)So we decided to enlist the help of this family member to list the condos through his office.

I doubt that master electricians get their license and then enlist.