As with any used vehicle, depends on who had it 7 how they treated it. I think 2006-2010 is the "previous" generation of the G/C (before the 2011 redo), you might think about one of those.
I got the 2004 G/C in mid-2007. It only had 28,000 miles on it and was pretty clean.
Never had any problems with it, though it was mostly a winter vehicle for the first couple years, then an every-day driver for another year.
Now I've had the 2010 for 20 months and no real problems here either. Minor issues with the navi/radio unit and the keyless entry.
The winters are sometimes extermely harsh over here. Good to hear that it can stand it.
Thanks for the tip mate, but the 2006 model way above me. I've got a budget of around 50.000 SEK ($7.000 USD) The cheapest Cherokee I found from the 2006 series is 135.000SEK ($19.000 USD)
I'd buy the 2006 model if i had the money, but with being a student, unable to work full time, the bills dont exactly grow on trees.
If your winters are bad, maybe look for a model with the "low 4x4" gear lever. I never really needed mine, but used it a few times to get out of being plowed in.
Just don't forget to change it back to "high" for normal driving.