I love your why, family and personal time are extremely important for us mentally.

I've always been really cheap when it came to buying cars because of the Millionaire Next Door mentality, but it got to a point where I was driving my wife insane because I kept on shopping for 10 year old beaters for my next car. 

So it doesn’t have to be 1 vs another sort of mentality, you can do multiple options. 

Its not paycheques it's the mentality that results from upbringing and society.

It is really messed up mentality that a government and it's citizens think that is ok.We had a week long family vacation planned in NYC for June 2020.

Just from your reply above I bet getting this weight off your shoulders would be huge for you mentally.

The fast money mentality is what caused me to lose so much in the stock market.

How does one get past the idea of NOT having a traditional retirement account and into the mentality of leaning on rentals to consistently bring in cash flow?

The velocity of deals being done can make  a difference in market cycles at various points in time.Buying assets with top market rents and high debt could be a bad thing as it saddles you with non-producing with loss or neutral debt load which can hurt ability by more properties.I saw in the last downturn of 2007,2008 where people had a buy anything mentality and the train stopped.

You need to buy some kitchen equipment, one or two of the good basic cookbooks like "The Joy of Cooking" or Bittman's "How to Cook Everything," and build a sustainable repertoire of 10-15 cheap, healthy dinners with a few variations each that you can put together easily and quickly.Better for your pocket, better for your mental health because it will help ground you, better for your love life because smart, capable people appreciate personal cooking skills in others.The top three expenses of the American household, as @Scott Trench's book taught me, are housing, transportation, and food.