Renovating both simultaneously.

If you are itching to get started and determined to lock something in during the next couple months, I'd look a little further out (but simultaneously do your best to save for that future primary residence).

For instance, it can quickly and simultaneously lower your expenses while increasing your income (the fundamental recipe for building wealth), you get the better terms of an owner-occupant mortgage, it can provide multiple exit strategies (rehab, sell, move out in a year or two and rent it, just keep living in it, etc.), and--importantly--it will teach you many of the most important skills that are needed for continued success in REI (e.g.; property analysis & due diligence skills, tenant screening skills, property management skills, etc., etc.). 

Maintenance, safety and late payment can hit you simultaneously.

First house was a "duet" where I used a second, simultaneous VA loan (since the CoL is so high here they DO allow it!).

However, with that same cash leveraged using hard money you can buy 4 flips simultaneously then you make $160,000 profit versus $50,000.

The biggest thing for me is to be able to quit my job, but I just can't justify doing it yet since I have good flexibility and still am able to run two other businesses simultaneously. 

Noorden...some title companies don't understand wholesaling.....and have never done double closings or simultaneous closings or assignments....they operate traditionally

Start looking for a property while building your team simultaneously.

I will say that one of the benefits of driving for dollars is that not only can you find some good leads to go after, but simultaneously you are learning your market if you are doing it right.