My '93 Jeep XJ (Cherokee) is at the point where things are failing unexpectedly (recently had the alternator seize, which lead to a blown head gasket before I could get off the road) and as much as I'd like to keep it going, with two kids, I really can't plan on being stranded.
The wife's Hyundai Santa Fe ('02 with less than $250k miles) will become my semi-daily driver (take the kids to/from school 2-3 days per week + get me to my Army Reserve Training weekends -- maybe 750 miles per month), so what we're really looking for is a new daily driver for her, that has good highway milage for road trips, (ideally) AWD and a decent sized trunk for suitcases for road trips.
We were thinking sedan, but since the Santa Fe is getting a bit long in the tooth too, we're looking for something SUV-ish. It doesn't have to be as off-road worthy as the Jeep, but we shouldn't have to worry about going off-pavement for camping trips and a tow-package would be nice just in case. We don't need to buy new, a 2013/2012 lease return wouldn't be a problem if they were good years for a vehicle that's been cheapened-up a bit for the 2015 model year.
So far, we've looked at the new Cherokee (Trailhawk edition), Santa Fe and Chevy Traverse. There's a lot of decent cars out there, but we don't have a good feel for what will last us until the kids are out of the house.
I think the new Jeep Cherokees look freakin' amazing, but I just can't bring myself to buy one. I can't help but think it'd be a valueless shitbox by the time it rolled 100k.
I went through this same thought process a while back and ended up with a Crosstrek.
Edit: Not much in the way of trunk space though - you might want to check out the Mazda 6 series.