If a bank sees you consistently doing profitable deals, that lowers their risk.Personal Property: if you're making the money, you'll get the loan for your personal property in 5-10 years.2 Years Performing Asset: what to keep in mind with all of these "rules" is that they usually reflect rules for a "conforming" loan, i.e. one that will qualify to be sold to Fannie/Freddie as noted above.

I paid cash for everything, it was a huge struggle as I did not qualify for financing.

Now I have been notified by the Section 8 administrator that she no longer qualifies for a 2 bed room apartment.

The lender is kind of a first step because they can help you know how much money you can qualify to borrow and that's what gets the wheels moving with being able to set goals and analyze properties. 

As experienced self-directed investor @Larry F. gave you some good tips, and it seems that you did a good job educating yourself.As a real estate agent and notary you are considered to be self-employed, therefor qualify for truly self-directed Solo 401k plan.

We would rent the front house out, and live in the back house, which I was hoping would possibly help us qualify for a larger loan. 

In other words he doesn't qualify for a loan.

I contribute the max I can to qualified accounts (401k, Roth IRA, HSA) for both myself and my wife and still have money left to invest personally.

You should speak to a lender first and see if how much in loans you can qualify for and then compare that amount to the neighborhoods and property types in Los Angeles.

You can shelter some of that if you run your business through certain entities, but in this case, it looks like you've got this one in your own name (because it was supposed to be your home)2) I believe the property has to be in-service as an income generating property for a year before it would qualify for a 1031.