I would like a payoff planner that helps me navigate the various maturity dates and interest rates of my (15 due in 5) mortgages so that I gain the best financial advantage when paying down principal balances. 

In theory it would be wonderful to get mortgages at 3.5% down and search for value-add deals to near break even on cashflow after year 1-2, banking on appreciation from a highly-leveraged investment in a growing economy.

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

Pay the mortgage.

At the time, PPR was selling courses for investing in distressed 2nd mortgages.

It is a duplex near scranton PA. the Mortgage is about $2,400 and each tenant pays $1,550 monthly in rent so I make about $700 in cash flow monthly.

Because jumping from a mortgage to rent does not really solve the problem.

Quote from @Brendan Jones: I am very new to learning about real estate and am looking for advice on my first home and how I can best use it to help offset my mortgage and generate cash flow.

While the 4% mortgage is great, your 1M in dead equity isn't giving you a great return.

Keep primary mortgage @2.9%, paying the minimum.