Since a family member is owner-occupying, this should be feasible.

The idea of having tenants pay for my mortgage while occupying one of the units.

He's helped us navigate a few tenant issues while selling occupied properties.

I file for "owner occupied" status and have the mortgage interest fully/partially deducted on my tax returns. 

My background: I am a new to real estate/BP and looking to score my first owner occupied rental in a highly competitive market (Northern Jersey).

It would be owner occupied (by me) indefinitely and I can rent or sell for a profit in the future.Questions on what I have proposed:1.

Househacking is definitely the way to go to get started... granted I was always told by mentors of mine that living in a property is ideal before going through with a non-owner occupied investment.

Are there any builder websites that might show a # of different property builds that might be optimized for something like owner occupied or tiny multi-family/duplex?

MIP is very high (I live in San Diego) and while I've only been in my home (duplex, owner-occupied) for a little over a year, I have made some upgrades and the local appreciation might have me at around 85% LTV. 

Buying investment property isn't different than buying an owner occupied house in terms of the steps so ultimately you just need someone competent, responsive, who you connect with and who does what they say they will do.