You do have one advantage of being able to conserve capital with a VA loan for your primary residence.  

On the positive side having MLS access is a very good tool to help you find and analyze and sell properties quickly for flips. so as you can see keeping them separate is the way i would go. so now on the investing side, again, what type of investing are you looking to do?

I stick to my criteria so never get first position, but I close in two weeks on a house because the offer they originally accepted fell through.

The first was a primary residence turned investment when I moved out and rented it so this feels like my first intentional investment.I am looking at duplexes and triplexes in the Philadelphia area [I'm from a suburb of Philly] and have been going right to the listing agents to schedule appointments to view properties since scheduling is a challenge with most of the properties fully occupied.

So my first priority is to get into my own primary residence.

Thank you biggerpockets community for the instruction and support that has allowed us to be in the position to need to ask these questions. 

People get this crazy idea that any property will produce positive cash flow and will make you money.

It doesn't change my position one bit, but I think you will hear some moaning and groaning a bit more than if you just had a family Park.

We are in a 1031 position until 10/3/16.  

We currently own our primary residence in Nevada, a vacation property in California and a SFR rental in Seattle.With our limited experience thus far, we are considering out of state properties in the $1-200K range.How long does it take before one could justifiably be considered a pro in the eyes of the tax man?