Based on how I am reading your summary it sounds like there is solid equity in the 2-family in order for a bank to cross-collaterize assets. 

I currently have a single family property averaging $330 a month in cash flow which is going into a basic checking account seperate from personal.

I've already paid for an appraisal and the earnest money is recoverable.Thanks BP family! 

Investment Info:Small multi-family (2-4 units) buy & hold investment.

Quote from @Francisco Pila: Quote from @Heidi Xu: Investment Info:Small multi-family (2-4 units) buy & hold investment.

According to the Planning Board, the intent of the RM-2 Zone is to create, maintain, and enhance residential areas characterized by a mix of single family homes, duplexes, townhouses, small multi-unit buildings, and neighborhood businesses where appropriate.I'm assuming by definition I am zoned to convert to a triplex?

Ensure you are buying in an area you want and can see your family living in.

Maybe a mom & pop owned small multi-family can owner finance or sell to you with some guidance for the transition.

Investment Info:Large multi-family (5+ units) buy & hold investment in Flagler Beach.

I know I could have a family member co-sign a mortgage with me but not sure the best way to approach that conversation and what incentives I’d be able to offer to make it worth while for them other then their “familial duties” haha.