Win/win for a small gamble.

I can't wait to learn and share my experiences with this site.The book "Rich Dad Poor Dad" ignited my search for financial freedom, a few finance and accounting classes later eventually led me to Bigger Pockets.I'm currently searching for my first investment property (2+ unit).

I do know that with this being my first rehab,it’s a gamble.

Its a gamble but most things in homes are. 

California is not the market for cash flow, it is the market for appreciation which is speculation (gambling).

Either  1) You have the money to be cashflow negative (including mortgage) for a hold and flip with appreciation (gamble) 2) If you had the skills, you could find fixer-uppers and flip or improve equity and hold (safer) 3) Or you could be new developments that are ready in 1-2 years and flip them which I have done quite successfully.

While we were never overtly irresponsible with money (i.e. gambling debt, drug habits, credit cards, expensive cars), we moved many times, did PhDs, and spent the better part of our 20's and 30's doing things that might have been personally enriching, but were at some level exploitative of our time and not financially beneficial.

This is perhaps a larger gamble.  

It requires extensive experience, but you have to be willing to gamble a little bit to be successful.

At that point you’re almost gambling on what interest rates and the local RE market is going to do.