I currently own ONE rental property which was a previous home 4 hours away and at the moment based on the numbers I have is slightly on the positive side of the cashflow equation. 

I usually equate the two, especially with the age of the home as negative.

I feel like this part of the whole equation is where I lack confidence to make offers.

This will equate to higher tenant turnover.

Wholesaler exist because they bring some value into the equation, if they dont then there wont be any wholesaler.

Don't discount the amount time you will have to spend in managing all of this if the tenant is not right and put that into the equation.  

And you use the ARV time .7 minus repair costs equation?

Also, I think there are enough moving pieces in your situation (your income, the income that is being brought into the picture by your wife, the connected-but-disconnected nature of your brother in the equation, etc.) that it's worth talking directly to an attorney and/or tax professional - given the money and complexity involved, likely best to get the *right* answer rather than a cheap answer from BP.

Where would you eventually like to end up and how would Portland, Austin, or somewhere else make sense in this equation? 

After reading further it seems 50% rule equates to 2% in order to cash flow and around 1% to break even.