I am going to be another vote for a Jeep. I am not a big fan of the 1st generation Liberties. The 3.7L is a big dog. Seems like it has much less power than the 4.0L. Interior is pretty basic. I hate where the window controls are. The newer Liberties are much nicer, but may be out of your price range.
I am a big fan of the Grand Cherokees. I have a 2001 Laredo with the 4.0L that I picked up about a 1.5 years ago. I got it for $5K with 111K miles. Only thing I have replaced on it since then are maintenance items, brakes, battery, alternator. Common problem with the WJ (99-04) is the fan relay for the aux fan goes out a lot. Easy to replace once you have done it once and you cut the panel. Normally you notice it in the summer when you have the ac on and sitting in traffic. The aux fan won't spin up faster to help cool down the engine, or it stays on high all the time. Other common problem is only on the Limited models, the blend door for the heating system will stick closed. Many write ups on how to fix this.
As for engine, I love the 4.0L but since I went to a little larger tires, I wish I had the 4.7L. Gas mileage is not that different between the 2 engines. Only thing is the 4.7L normally comes with the full time 4x4 system. I love having the selectable 4x4 system on mine so I can run in 2wd and then pop it into part time 4x4, locked high or locked low if I need it.
I have also been looking at a few newer Grand Cherokee's (WK 05-10). They are a much nicer ride than the WJ and have a lot more options for the interior, but they are probably going to be a bit out of your price range.