We built it out of necessity and started same way as everyone, cut our teeth on bad decisions.

I am not going to move into a dormitory style house and raise my two year old in a location with poor schools and incredibly dense housing, unless I have no other option. 

You get as much objective information about them so that you can make an informed decision. 2.

Turned a single family house that was poorly marketed but in a great area of my city, listed mid-winter where there's less competition, into a duplex for all intensive purposes and used airbnb to rent out rooms.

@Chris Kay beleive you can do DSR loans without a job as they qualify the property, not the borrower.You'd still need 20-25% down though.That's where you have a decision:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- Save up for your next acquisition.Only YOU can make that decision as you have to be comfortable with the increasing debt-load risk and the additional time to manage everything.

Sure, I'd love to win the Mega Millions and have millions of resources to make certain decisions, but the reality is I want peace- in knowing obligations aren't something to worry about. 

And then get to a decision quickly.

I have San Diego properties purchased with good timing and properties purchased with poor timing.  

This was my first property, and while it's been a great learning experience, I made several mistakes along the way—ranging from choosing a realtor who was more focused on closing the deal than finding the right house, to having a poor inspection and overlooking issues hidden beneath the surface (literally).

This outlook is reflected in the prices resulting in poor initial cash flow but historically great long term cash flow.