I am currently looking to utilize my VA Loan for a small multi family (preferably a triplex/quadplex)  house hack one unit, and hold the property as a cushion to stabilize myself in my real estate journey.

In my personal preference I would be inclined towards the 2nd route for the time being, which would allow you to make a friend successful AND you would profit nicely. 

Here's an example, pardon the formatting as just copied and pasted ours.Home Address*Occupant Names*EmailCell Phone*Home PhoneWork PhonePreferred Contact Method*Preferred Contact MethodPortalEmailCellHomeWorkHow much is your rent?

@Greg Weik i prefer getting paid directly from uncle Sam, than chasing a tenant for rent money.

Also yes, I would prefer to be  close to my properties as I do self manage for now.

To maximize full value, most buyers do indeed prefer for the property to be vacant.

I'd prefer to do that over renting out of state depending upon your situation of course. 

Your attorney(s) should be able to advise the proper location and structure, which may vary from state to state.While there are reasons to go wider, I suggest you narrow down to a couple of states or preferably a smaller area than that.

When I asked him why wouldn’t they just stay at MGM like a normal person, he said there’s this group of people who prefer the privacy of a non-commercial property lease.

Some 4 units in my market start around the $200k point so could even buy 2 of those instead of 4-8 single families.It’s all your preference based upon your goals, but overall the Midwest is a great market.