Hi Neighbor.
My husband has family that work in manufacturing for each of the 3 Detroit Autos. I would not purchase a Jeep with 100,000+ miles. If you do go with a Jeep the Wheaton dealership has a MUCH better repair shop than any of the others.
I looked at a brand new Jetta the other day they start at $15,000--I know it is more than you want to spend, but its brand new.
Send me a PM if you want some other ideas.
This is a lot of what I'm doing. I was looking into the Jeep line, either Patriot, Liberty or Grand Cherokee, in the $15,000-$20,000 range. I LOVE SUVs! My previous vehicle was a 2002 Land Rover Discovery but I sold it because I didn't need it and it killed me in gas.
Part of my decision making must include gas mileage. To get from my house to school is about 30 miles each way through rush hour traffic, and add other stops and places I need to go, it's ends up being about 80 miles/(week)day. So while I'd love to have a Grand Cherokee or Liberty, they take too much gas. Plus, the GC usually comes with 60,000 miles+ for my price range.
The Patriot is better for gas at about 22/26 but, it's hard to find one with features I want, and are important to me such as AUX & power windows/locks. So I can either get one for dirt cheap (relatively), the one I've been looking at is 2010, used with 1,000 miles on it, for $15,998, but it's without many features. Or closer to $20,000 with around 50,000 miles, more features, and an older make.
Hm... then I look at the Jetta. Newish, 2007-2009 models, less than 30,000 miles, all the features I want and then some, and all from $12,000-$15,000! Not to mention much better gas mileage. And, I'm pretty sure it's going to last me longer

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I don't know why I felt I needed to tell you allll of that, but I think I'm in a similar predicament as you.
Another one I've been looking into is the Dodge Caliber. But while I can drive stick, I don't want to, and most of them that I can find come in manual. But they are definitely a cute car. I like to think of them as mini-SUVs.