The value adds and the market appreciation profits pale the cash flow (this is even with a duplex that cash flows over $5K/month).

I suggest talking with @Connor Gillen who has a strong grasp of the market up there

Should I really just be leaning on a local real estate agent to help me with the local markets?

Would really like any insights you all may have on the potential (if you have worked in them) in these markets and if you feel there is opportunity in all 4 stages of our strategy in that city. 

Would sec 8 decrease the rent to the calculated fair market value of rent or at worst case scenario remain the same and sec 8 decline the increase?

You can invest in any market selecting the ones that you believe are seeing the most growth, and do it from anywhere.

If you're looking into your next market, I would recommend Columbus Ohio.

You will gain so much knowledge from the experts in your market and also may find someone who is in the same boat of you.

I'm particularly passionate about cultivating an extremely tenant-satisfaction-focused mission in order to distinguish myself in the rental market. 

Springfield MA is a great market for rentals!