I don’t love this example because enjoyment of the object isn’t really a cost. If I buy a book or a videogame or a movie, the time it takes to enjoy the media is the value, not the cost.

If you’re talking about maintenance and upkeep on your car, that is a different type of cost that has to be weighed against the cost and time expenditure of a bus pass or whatever your alternative was.

In other words I feel like this is a catchy phrase that kind of falls apart once you start to dig at it.

I feel like there’s a lot more to this than “pay it twice”. If you’re talking purely in dollars, then you’ll want to consider maintenance and upkeep over the expected lifetime of the object and compare that to alternatives. Additionally, everything has an opportunity cost because no resource is limitless and you could have allocated it elsewhere. Finally, emotional and other intangible benefits are something that most people have a very difficult time quantifying.

If you want to say “consider more than just the purchase price” then I’m with you.