Many of our investors will do a cash out refi after a brief seasoning period, and are able to draw cash out to buy their next one.As @James Wise pointed out, investing OOS is not that scary if you work with the right provider. 

Time wise, a flip from start to close will be 4-6 months where a new build is more like 8-10 months.

Would I be wise to try a couple other places for financing?

Steer clear of financially irresponsible people that have debt, choose your partner wisely and they will be a attribute.

But, with wise decisions you can pick a good rental.

I've been working on ways to start the ball rolling for my real estate business (money-wise) and I came across what I think is the perfect fit for me to get funds quickly to start BRRR-ing.

In my situation I would THINK that since I lived in the property first, then rented it, as long as I move back into it and live there long enough to satisfy the 5 year look back, I'd be good to go exclusion wise. 

Which of these judgments should be paid ... a judgment to James Wise, James Wise Rentals, LLC, neither or both?

I appreciate the advice @James Wise, I'm not familiar with the kind of stigma wholesalers may have but i suppose i'll come to learn that with time.

I will need to pay off the existing mortgage ($451k) with a construction loan; at most I can put in $180k toward the build but not sure if that is wise to put so much of my own money in.So far my best option seems to be to partner up with an experienced developer/builder who can put down cash towards the construction downpayment *and* qualify for a bank construction loan.