I wish you the best in your endeavors!  

Would love to connect with each of you and learn more about your endeavors.

However, if you had the resources and are willing to commit, I'd say you could in theory skip the SFH all together and upgrade but knowledge may be what kills you in that endeavor, so a savvy, veteran partner would be a nice addition.

You definitely don't want to over-leverage, but this is a historically great time to borrow money on cash-flowing assets, and leverage is the special sauce that can transform real estate from merely cash flowing to multiplying your wealth.  

It seems that I can't go the conventional loan route under my personal name because I have no W2 income since I was self employed for the last 10 years and I have been transitioning out of those business endeavors for the last 2 years therefore I have no real income to show.

I hope this info helps you in your endeavors

A "successful" flip is subjective -- beauty is in the eye of the beholder -- I would assert that any business endeavor is successful when you exceed 20% cash-on-cash return. 10% would be adequate. 5% would mean you barely scraped by.

That will help me build cash for true REI endeavors.

Good luck and may you have success with your future endeavors!

As you start this new endeavor, I would highly recommend sitting down with a mortgage/financial professional to come up with a plan to help you achieve your short-term goals that will give you the proceeds and resources to pursue and achieve your long-term goals.