I don't know if/how doing multiple refinances in a short period of time will impact your loan eligibility. 

@Ronan M. thanks for that question.GC Realty & Development, LLC has coverage in the Western & Northwestern Suburbs of Chicago plus multiple neighborhoods in Chicago including Washington Park, Greater Grand Crossing, Hyde Park, South Chicago, Deering, Calumet Heights, Hyde Park, Bronzeville, & Woodlawn.  

Title report I have access to shows it's a duplex but everyone involved is telling me its a Tri.

Usually when a seller wants to sell he wants to SELL and won't entertain efforts involved for a lease purchase.

If you have one meter for multiple units then Landlord pays and rent price may be higher due to this.

Looks like my next steps are to get involved with REIN and to keep reading up.

Then offer, if they have any other needs in their business, that you're really hungry to get involved and to learn the business, so if they needed help answering phones, cleaning toilets or whatever, that you'd love an opportunity to work with them and help out. 7.

Take this all with a grain of salt, but to me when the conversation involves house hacking in an expensive metro area like NYC/NJ the bigger picture is more important than the immediate short term cash flow. 

Is it better off doing that or just getting your own people involved.

If you want to 10x yourself, thing bigger and more creatively....and consider hiring a coach in the area of your focus (see links - first one is from my coach on ways to get into MF investing; the second is an interview I did to share ideas on how I got involved and accelerated my experience, learning and income).