Areas like Lawrenceville and East Liberty have undergone huge transformations.. it’s worth exploring how those shifts could affect your property’s future value.What’s your take?

I doubt he'll be able to quality for a loan (VA) with just his income. 

Private mortgage insurance i believe is not charged on va loans.  

Rent for a few years and convert to primary.Next Step/sHow do we shift while keeping AGI at lowest levels?

It's a VA loan, so long as someone can meet the requirements.I have it as a subject to, subto, so it can be done with creative financing too. 

A lifelong friend and I are motivated to (virtually) meet and connect with those in REI working in the Pittsburgh area.I'm active duty military and living in California with two rental properties (one in Virginia Beach & one in Pittsburgh) and my close friend owns a single family in Baltimore.  

If I rent it out, I'll be hiring a property manager because I don't want to deal with trying to manage it from out of state.Some numbers:Purchased with 0% down VA loanPurchase Price: 189KMortgage: 172KRate: 2.25%4 Bed / 2.5 Bath~2400sq/ftBuilt in 1992Zillow Sales Estimate: 280KZillow Rent Estimate: 2,100/moRoof and AC are less than 10 years old.

And, considering market shifts.. what’s your approach to minimizing risks over the next two years? 

It recently dawned on me the idea of a non military affiliated individual assuming a VA loan, would this individual be able to then also gain the benefit of using an IRRRL since they have now acquired a VA loan through assumption?

Yes, you could use your VA loan.