My wife and I traded our 97 Outback in on our 05 Pilot. My mother-in-law has a 02 Outback, so we have experience with two of the last three generations of Outbacks.
We've been extremely pleased with both cars and the 05's look to be very good as well.
We ended up choosing the Pilot because of the added room and the ability to have a third-row seat. The extra towing capacity was a plus as well.
I haven't driven the Pilot in bad weather yet, but I think the Subaru AWD system is the best out there.
If we didn't have two little boys in car seats, we probably would have gone with another Sube, but are really happy we bought the Pilot.
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