I keep going back and forth when I think about my next vehicle. This is a problem, since my current vehicle really does need to be replaced in the very near future.
I have a choice between purchasing an older, less expensive vehicle, or a newer, more expensive vehicle. On the one hand, I have really enjoyed not having a car payment and a the less expensive vehicle would be much quicker to pay back off. On the other hand, I can't get the vehicle I want for the lower price, plus the newer car is less likely to have any repair costs for the next several years.
So I'm in this unfortunate circular logic spiral where I keep weighing the pro's and cons. And I have to be honest, the only real pro to going with the older car is that I won't put myself back into deep debt immediately after getting myself out of it. But that is actually a fairly significant mental issue. I hate being in debt, and have been looking forward to doing something with my money other than paying off debt. Plus, I don't like the fact that when you buy via car loan, you end up paying a hefty chunk to the bank in addition to what you pay for the car. Plus, since I'm looking exclusively at toyotas and hondas, I don't have as much concern for the mechanical problems, though individual cars do vary fairly significantly.
But it would also be nice to drive a car I actually want to drive. When I owned my Rav4, I enjoyed driving significantly more than I have any other vehicle I have owned. Plus, spending a bit more for a lower mileage vehicle still means I would get the long life that comes with toyota/hondas, its just that that life would be even longer than the higher mileage vehicles. Plus, since I'd own the car through most of that life span, I would know that it was well maintained and cared for, instead of it being a crap shoot. In the end, it really comes down to this: Is it worth the extra 4-9 thousand dollars to get the nicer vehicle? (the range comes from my two price ranges. At the low end i'm looking at 6-8K vehicles, at the high end, I'm looking at 12-15K vehicles).
I just wish I had an answer to that.