New or Used: It's Hip to Be Square?

TTAC commentator Philosphil writes:

Hello everyone,

I’m looking to replace my 03 Jetta wagon soon and have test-driven many vehicles. I have periodic back issues and so want a vehicle that has easy ingress and egress (so that ideally I neither have to climb up nor drop down when entering or exiting the vehicle). I’m about 6’, but have a relatively long upper body. I’m also looking for something in the $17,000-$20,000 range (Cdn, or about about $15,000-$18,000 US). Of the cars I’ve tested so far, the ones that seem best suited to my needs are the boxes (to my wife’s dismay–they tend to have the largest opening between the driver’s seat and the top of the door sill). I would also like to keep this car (and actually like it as well) for 8-10 years.

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