I don't have the cash required, so I'd have to finance.

Removing any appreciated property from an S-Corporation triggers a deemed gain on those assets by the S-Corporation (hence also by you) - it's as though you sold it at fair market value, so you get the joy of paying the taxes on the appreciation while receiving no cash. 

Purchase price: $50,000 Cash invested: $30,000 First BRRR property.

And is it better to be cash flow positive vs have more cash in hands ? 

I cannot wrap my head around the cash out refinance portion of this situation despite my tireless efforts.

Cash out 3.

They help with money control, lead to wiser choices, and track cash flow better.

My car payment is pretty reasonable ($366/month) so that wasn't in my original plan and eats into my cash for furniture/incidentals. 

Purchase price: $2,225,000 Cash invested: $350,000 Purchased a 40k sqft ft mixed use building on Main st in Middletown, CT.

If you have a $1,500 or more spread between cash flow and living expenses, I would consider saving the rest to add to a cushion.