Done a couple of flips, currently working on one that I’m considering to brrr it’s a single family 3bdrm 2 bath.and hoping to get a multi unit next. we are very skilled in the construction end (have a hardwood floor business) new to the nuances of rentals especially in New York State .

It certainly could improve your cash flow but it won't help with finding prospects, screening tenants, maintenance, deposit dispositions, etc. 

The GIS map designates it as a single-family dwelling, but the property is clearly set up as two units, with separate HVAC, electrical systems, etc.My main question is: Would it be possible to obtain a permit to legally convert it into a two-unit property?

We are excited to get started but want to make sure we set ourselves up well by talking to folks in the field to set up our business model well, find great real estate agents and investors that work in our area, and see who else is out there doing it in this area.

Better off finding a small GC with  a small crew you can book time with. 

Does bigger pockets have the tools for me to find investors for when If when I land a deal?

It's possible to find them without prepayment penalties, but the tradeoff will generally be a higher interest rate and/or additional fees (points). 

Do a Google search for "Boommates" and you'll find references to the Golden Girls TV show and discussions about two significant issues older people face: the high cost of housing and loneliness.For younger people, we call this "house hacking," where someone buys a house and takes in roommates to help cover the costs.

Curious to see if anyone on here has had any luck finding one?

There are some that will post on the Bigger Pockets market place but you'll find tons of them on Facebook.