The next steps in my mind are; contact mortgage broker to start steps for financing, get stamped plans for what I want (I assume the people lending me money would like to see what i am trying to do), while simultaneously getting my contractor on the same page.

I, of course, would love to also simultaneously build my portfolio over time.

Simultaneously while this was occurring I was still marketing the home on facebook, contacted realtors, hard money lenders, we buy your home for cash people and land lords but still no offers.

Let the risk sit with the 2nd home and hopefully you get a good enough deal that the family members can cover the mortgage and expenses on it while you sit back and wait for it to appreciate and simultaneously reap the benefits of loan pay down.

To answer your other question, in marginal or difficult eviction communities, you will see either less rentals or more initial and ongoing cost borne by the tenant, or both simultaneously.

That said, there's nothing wrong with simultaneously putting together a buyer's list while looking for a deal but in order to move from the theoretical (i.e.

As a long time real estate investor I have constantly surrounded myself with real estate, even while simultaneously working in banking and financial services.

Community property with right of survivorship should avoid probate at the first death, but what happens at the second death, or simultaneous death like a car accident? 

It's not a chicken and egg situation either way, you have to do both simultaneously.

That is, with both happening simultaneously where might I get hung up?