I bought my Outback Wagon (OBW) in April of 03 with 42k on it. At the time I was unaware of the dreaded head gasket problem! Mine had the AT and the "Rocky Mountain Edition" package which included heated seats, mirrors and wipers. About that: the only seat heater that worked was the driver's side. As near as I can tell the mirror and windshield wiper "heaters" do absolutely nothing. Either that or mine were broken. Lots of fun to drive, especially on dirt roads - it's fun to play rally racer in this car! Ground clearance is better than average at about 7.5" but this is not an off-roader. Mud can get packed into the driveshaft tunnel. Has a lot of capacity. Good car for the money.
I never had any serious trouble with mine but was always worried about the head gasket, which is why I sold it at 120k. Economy was good at 23 city, 27- 30 highway (AT.) AWD is a blast and worked great in the snow and ice of Wyoming and Colorado. Almost long enough for me to sleep in.
Driver's seat is not comfortable on long trips, padding crushed down. Beware of the dreaded head gasket! Best suggestion is get an 03-up model, you will have no HG problems and you will get the rear limited slip, too (not avail. in '99.) Don't expect seat, mirror or wiper heaters to work.