So for anyone who has made this change before, with a wife and a newborn, I would love to hear some of the challenges you experienced and how you were able to overcome those challenges to achieve your dreams.  

One can dream...

Anyhow, what I'm doing in BP is trying to learn as much as possible, find knowledge, share personal projects, get/give advise whenever possible, make connections, all in line with making my dream possible one day which is to run a small family run investing firm.  

I have aspirations of flying for the airlines someday, but I also have aspirations of developing a RE portfolio that produces around 10k a month so I can have a FI lifestyle and live out some of my other dreams.

Where as if you can buy your dream home for 180k and ya know you wanna live there forever.

I read on some other discussions here that positive cash flow in San Diego is a dream on any new properties so does our current strategy of buying and holding still make sense here?

This leads you to overleveraging territory, so you ought to measure whether your dream factory job can support the maintenance of however many units you are looking to purchase on top of debt payments on both a HELOC and mortgage.

I believe that most people on here are of the entrepreneurial mindset and would benefit greatly from starting another dream business in one of these Opportunity Zones.

Nice to see someone pursuing their REI dream with focus & a strategy.

He doesn't want to deal with the properties any longer and live the dream?