I've had a 1999 Jeep TJ for the past 9 years and for the most part I love it.
A few things you'll want to know...
1) Gas mileage sucks. I get about 550 km on a 62 L gas tank, doing a mix of city and highway driving.
2) Jeeps have the aerodynamics of a brick. Watch out for wind gusts.
3) The brackets that hold your side mirrors and the hinges on your back window are made of some crappy white metal that won't hold paint and quickly becomes pitted with corrosion. The hinges will crumble to powder over time and are expensive to replace.
4) The radiators typically need to be replaced after 9 to 11 year range.
5) If you're over 6 feet tall, then the lack of leg room can be a pain. When I'm travelling long distance I typically have to stop every couple of hours to stretch my legs.
In closing, Jeeps are great in winter and they are a dream to park due to the short wheel base.
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