The requirement was introduced in a phased approach with some zip codes earlier than others (not entirely sure the policy consideration behind that approach), but now is required throughout the city.

By my count, that's probably close to $1,000,000 in non income/cash flow producing debt. 

I would also give this podcast a listen to give you some ideas from somebody who was in your shoes 10 years ago.Financial Freedom in 10 Years and $200K Cash Flow (biggerpockets.com)

I have identified some properties that could cash flow well, but only on creative financing terms and looking to understand how the deal can be structured (1 seller is definitely willing).

No, that's not included in my cash flow.

I understand that each market offers a unique perspective.As of now, my goal is to have cash flow as I focus on CoC return. 

Hello,I am looking in Gardner, MA for my next investment and seems like there are quite a few cash flowing properties out there. 

However, as long as your real estate investments are covering debt service at 1.25x or greater, it will wash out the DTI impact in residential lending and blend out in your global cash flow / debt service for any bank  or commercial lender. 

Is cash flow the main objective?

My current flow is 1) find a house that matches the configuration (X beds, Y bath)  in a certain neighborhood (Redfin or my agent)2) pull up rent data in rentometer / Zillow 3) run through my spreadsheet with expenses, taxes, insurances and etc I would love these to be automated.