Since I just traded my T for an H2, it will probably be a few years before I buy a new vehicle for myself. As I've mentioned before, I really hoping GM steps up to the off-road plate and comes out with a Tahoe/Yukon with real off-road ability. A selectable locker or two, 33" tires possibly with room for larger without a lot of fuss, a bit more ground clearance and decent skid plates. That's really all it would take for me to be ready to trade my H2 in on one. Well, that and having them hit the used car market - I just don't buy new cars anymore.
The wife on the other hand... When my oldest turns 16 in about a year and a half he gets her car and she will be buying something else. Top two contenders right now are an AWD ATS or an AWD Audi TT. We've had a loaner CTS a couple times and she's taken it to work a few days.. We both agree, great car but just a little too big making the ATS seem about perfect. Unless she goes for the top down two seat option of which the TT is her first (and my last) choice. We keep our money somewhat separate and have divided up the bills in such a way that that she pays the car payments (including my H2), so she pretty much gets whatever she wants. When looking for her current car she was looking at CTS', BMWs (she hated them), A3s, S3s, TTs, etc. Apparently she got tired of looking and just came home one day with her Subaru Legacy. Would have been a CTS, but the AWD versions had only been out a year or two and were a lot more expensive than the Legacy.
Semi related - my plans for this spring are to sell my Corvette and use that money to get my Celica back on the road. If I can get it reliable (stop over heating) and maybe put in different seats it will immediately become my fair weather car.