I love the Outback - what a great wagon-ny alternative to an SUV. We briefly owned a 2001, but the missus didn't like driving it, the glass area on the Forester was much more suited to her, so we sold the OBW and bought the Forester. I like the OBW a lot, and even the new "size mucho" one appeals to me.
But, yeah, the long term ownership experience is a bit of a gamble.