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

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. 

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.

Not saying all tenants are bad, as most of us just want to make our rent payment on time and live our lives - but don't be surprised if you run into more headaches vs. spending a bit more money up front for peace of mind later on with placing better tenants. 

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.

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. 

Purchase price: $140K% Down: 25% (I am considering pitching the investment to a friend and making this a cash purchase - any advice regarding this decision is much appreciated!)

Might be a good way to get your foot in the door, not having to partner with anyone, low downpayment and a cash flowing asset.