I think this will be the short term realization, and anyone that did not wait on the sidelines and jumped in with the intention of a short-term re-fi might have to tap out. 

@Muhammad Kashif Flipping a property in 6–9 months results in short-term capital gains, taxed as ordinary income (up to 37% federally, plus NJ state taxes up to 10.75%).

Keep learning and determine your long term goals.

Some/many lenders don't like a 2nd mortgage behind their first (like the skin in the game), however there are both bridge or permanent financing options out there allowing you to leverage anywhere from 90% CLTV - 100% CLTV, but don't expect good terms...

The East Rock area of New Haven (near Yale) is a huge outlier in terms of pricing, very expensive. 

Sometimes a 5-10 unit DSCR loan is solid terms, but I'm quoting 7.4% ish for 5+ unit, DSCR.

Looking for guidance on the best way to proceed going forward in terms of asset protection and how to structure all of this real estate… 

A 4-plex would be ideal and you could play around with doing 1 long-term, 1 mid-term, and 1 short-term, plus you, if it works on your area to upgrade your income.

Both options have pros and cons, and the right choice depends on your lifestyle, experience, and long-term goals.

When somebody asks for advice, I always try to put myself in their shoes and understand who they are and what their objectives are so I tried to do that with you with the little amount of info I could garner from your profile.