No prison sentence for a car payment Brian. I created this post for fun and to get a pulse on the financial mentality of fellow RE investors. That you have been successful in the car care franchise and restaurant has blessed you with I imagine, significant amounts of cash to allow you to purchase a stable full of nice vehicles. Congrats and enjoy the fruits of your labor.
For me it's more economics - I really can't afford $500, $1000, $1500 monthly car payments and stay in the black. Would I like to own a fancy new car that can outrun anything around - absolutely. I'm just not there yet. So what motivates me? For me it's the ability to have the financial freedom to do whatever I want with my time (family, travel, volunteer for a worthy cause, etc.) and know that the passive income from RE is funding my lifestyle for the rest of my life.
You're the carpe diem guy - live for the day! Nothing wrong with that. I actually take pride in my modest choice of vehicles and think it sets a good example for my family (with 2 kids 11 and 13) to live within our means. Trying to keep up and get ahead of the Joneses - not my thing. Counting my Benjamins rolling in 24/7 - that's what motivates me.