In the end, there are only so much funds to access and invest and maintain a healthy debt to asset ratio.Ideally, given how amazing the SF Area is, you should be holding on to all your Bay Area assets for the longer term but I feel at this point in the cycle, best to cash out and buy your dream home that suits your family needs.

It's been a long road I spent 6 month in th hospital, and I saw many people with injuries similar to mine simply giving up on their dreams or life in general so part of my motivation is showing people in a situation like this that it is not the end of life it can be seen as a new beginning. 

Indeed if my career had started 5 years earlier it would have feen far easier to get into the market as my income and savings really only hit a good place around 2014...This summer we purchased a rental home which will eventually become our primary residence for more than I would have dreamed of a few years ago and in the end we had to ask ourselves two questions.

I have no doubt all your dreams will come true!!

They don't know that I dropped out to pursue this dream of real estate investing. 

My question is: Would it be better for me to get the free degree and pursue the CPA first, or take the real estate accounting position that will more directly relate to my dreams of being a real estate investor?

its been a lifelong dream of mine to be in ann arbor

This is coming from the owner of a plumbing company who has seen buyers dreams turn into nightmares behind this stuff. $10k-$12k sewer line replacement 6 months in will kill the “our new home” mood real quick.

Our dream situation is to:- Have a place to call our own whenever we want to be there (ie...cannot have a long term renter in the property because it defeats the purpose). 

I understand the basics of it but I actually want to get started and pursue my dream of financial freedom.