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

Cash out 3.

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

@Jill Barrett start networking with other investors in the UP here on BP via search feature.Ask/pay an agent to generate a list of all the houses in an area you define have sold for cash in the last 12 months - pretty good sign an investor bought it.

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.

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

The lender that I'm choosing to cash out with requires a 6-month seasoning period.

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

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