My vote is for the Legacy. I had a '95 LS wagon that we had to get rid of (family didn't fit anymore!). The AWD was great for dirt roads, snow, and even light off-roading (trails). The LS had all the stuff we wanted, power everything, cruise, air, sunroof, roof rack. The 2.2L seemed to have plenty of power too.
We didn't have to do any major maintainence, but we did have the timing belts replaced at 65K as preventive maint. Otherwise it was just regular oil changes, and tune-ups.