Crowdsourcing New (Used) Car Suggestions (UPDATE)

So, I am in the market for a new (used) vehicle, and I want to crowdsource some suggestions.

I am currently driving a 2006 Jeep Liberty with 90k on the clock. It was a hand-me-down from my mother-in-law to my wife. When my wife got pregnant, I sold my Jetta (2.0T) to buy her a Subaru Forester and started driving the Jeep. Overall, it’s not a bad vehicle, especially during heavy west Michigan winters. But, I do have some complaints: poor mpgs averaging about 14-16; very loud (I think my transmission, transfer case, and/or differential needs work); it doesn’t have enough room for two adults, a baby, two dogs, and all the luggage/gear; and, being a mid-00's Daimler/Chrysler product, the build quality is poor (I already had to replace both front doors due to rust, and now the rears and rocker panels are starting to go).

Thus, I am in the market for another used car to replace the Jeep. I am enough of a motorhead that I want something that is in someway “interesting.” Not necessarily fast, or cool, or sporty; but at least interesting enough that I can take pride in it. I am also now making enough money that I can afford a little more. We’re not talking Audi/Mercedes/BMW money, but I am not looking for a $5,000 craigslist special either. Can you help me identify some vehicles that I might not have considered?

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Here are my requirements:

  • Used with less than 50,000 miles
  • Four doors
  • Room for 5, plus luggage (SUV/Wagon highly preferred)
  • AWD or 4WD
  • Reliable with reasonable maintenance costs
  • Late model (needs to be safe for baby)
  • Under $25,000.
  • Something interesting about the vehicle that I can take some pride in.

So far I have considered Cherokees (especially used Trailhawks), Grand Cherokees, Audi Q5s, VW Tiguan and Touregs, Subaru Outbacks (3.6Rs only), and Ford Explorers (with the twin-turbo 6-cyl), and Volvos wagons/SUVs (but these are hard to come by with low miles in my price range).

I am open to all suggestions.

Flying Lancia Stratos for your time/suggestions:

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UPDATE: Going today to pick up a 2014 Cherokee with 31k miles, the 3.2 6-cylinder, and the Active Drive II system. Only catch is they need to address a warped front passenger side brake rotor before I buy. I had them agree that they would reface or replace the rotor (depending on service recommendation), and that I would be taking it for another test drive before signing the deal. They gave me a good price and about $1,000 more on my trade than I expected, so I am pretty happy overall. It even has about 8 months left on the factory driveline warranty.

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