Maybe buying and renting ice cream shops in rural North Dakota is your thing.

The Subaru is worse in every way (comfort, heat/AC, acceleration, build quality, ride, interior noise etc.) but I need it for the long, cold (-50F to -30F) winters and pure ice roads.

If you can cash flow from house hacking then that is icing on the cake.

I reached out to a family friend who owned an agency and was about retirement age and struck a deal to buy him out.

It's just icing on the cake.

Your question definitely struck a nerve with a lot of people whether they like to admit it or not, but this is something we all have gone through to some degree or another.  

I view my 401K as icing on the cake.

Most successful REI have their personal finances basically in order (the "101" level stuff, like 1/3 of income on housing & not having a ridiculously expensive car payment) before getting into real estate investing, they don't get into it with two nickles to rub together as some sort of "get rich quick" scheme.If we're following that 33% rule either way (rent v own), then homeownership then becomes more of a family lifestyle choice than an investment strategy, though if you get lucky with appreciation like @Jay Hinrichs that's certainly icing on the cake too.My $0.02 as someone that looks over a lot of people's personal finances - successful people, and otherwise. 

I’ve made two “Best and Final” offers and one initial offer, each for over $20 million, in between walks down the beach for lunch or just to get a shave ice.  

For many of us, the natural beauty, the job opportunities, the weather, the diversity, the liberal mindset of people etc. are an icing on the cake and trust me that icing is awesome even if it costs an extra dime or two.