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

I would like to build several (2 - 6) "shipping container" type homes for either short, mid or long term rental.

It’s something we’re still investing time into researching, but that’s all I can say right now.

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...

@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.

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… 

Quote from @Scott Mac: Safety - Inherit a fully paid for SFH, in decent condition, in the neighborhood you live in, and rent it out to long term tenants who you are comfortable with.

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

The title says it all - I am trying to find and talk to flippers in the Colorado Springs area.