But that will keep your VA loan tied up until they sell or refinance (pay off).

Even if you're not positive you'd win in court, it's going to tie up the property and the earnest money, which should be enough to strike a new deal with the seller that avoids that...

In other words, if you don't have your VA loan tied up in a property, and you are otherwise eligible, you can buy a property with zero down payment with basically no loan amount limitation set by the VA.

If I do owner financing now, can I get a mortgage in the future to cover the remaining balance of the loan?

It ties in well with investing when you've got an interest in both, but there are plenty of Realtors who don't invest and plenty of investors who aren't licensed.For me, the two go together extremely well and I'm happy I got licensed.

I’m trying to figure out if I can cash out refinance to an 80% LTV conventional loan on this type of property or should I refinance down to what the remaining balance is and then do a HELOC to pull out the rest of the equity(I’m not sure if that’s even an option).

You would take $500K in boot and would then need to purchase at least $700K of real estate using the remaining proceeds in order to fully defer the rest of the tax.An awesome strategy! 

The location, property type, and price-point may differ but what remains the same is what you already eluded to... you still have to go and find the motivated seller...Find motivated sellers.

*From people who invested before 2008 and after* what were your investments/strategies that remained strong during the recession or kept you afloat?

This ties up any loose ends and allows us both to move on.