Re: used car prices: I bought a (new) honda fit in 2011 - my first car, after 8 years of city living that I spent on a bike or a subway. I wanted to find one a year or two old, maybe save some money, etc (I wasn't a MMM reader, but I was in the right mindset!) At the time, I got my new fit for 1.5K more than cars that were two years old with 30K miles. I thought that 1.5K savings vs two years of car use probably wouldn't even out. As it turns out, our "new" fit now has 30K miles on it, but it took almost 4 years!
Re: the fit being a "shitty" car: I really have to object. I love it. It fits everything I need it to, parks easily, is good on gas, is reasonably comfortable to drive, gets us where we need to go, doesn't cost a crazy amount... PERFECT.
To be fair (and let's try to be fair): there are places where we all drop extra money for things that increase our quality of life, right? MMM travels, and a lot of people are willing to work longer to be able to afford to travel once they're retired. Hell, most of us could say 'I'm going to go live in a hovel, never buy anything ever again, and live on rice and beans' and retire this year, but we chose not to because the point isn't to live in poverty and misery, the point is to identify the sweet spot of how much awesome living you can get for how little money. We just each have to find what we value, to ensure that our money goes towards things that bring us rewards rather than being pissed away for things we don't care about.
Personally: my car is a depreciating asset and a tool to get me from point a to point b. I'm not a car person. However, I AM a food person. Fixings for a 5-course dinner including a roast duck because "it's saturday and I feel like it" is absolutely something I'll spend on. So... it depends on your personal priority. If you're going into it saying "this will make me work X number of weeks/years longer to sustain this lifestyle" and you're ok with that bargain, then why not, y'know. You just can't be blindly wandering into it and spending money on things that don't matter and trading away years of your life and time for things you don't care about.