I actually went from an old ugly station wagon (a Falcon EA Wagon) to an Outback. The Outback is not very large compared to traditional wagons and much higher off the ground. A few thoughts on a 1999 Outback vs a 1988 EA Falcon Station wagon:

The rear of the Falcon was so wide it could take a full (Australian standard) pallet in the trunk with the back seats folded down. I assume it was designed with this in mind and I was called on to move pallets at my work a lot in my younger days thanks to this car. The Outback could not do this. There's far far less space and the wheel wells on the Subaru are huge.

The Subaru Outback also objectively had less power than the older EA falcon (165hp vs 186hp) was higher off the ground and had AWD. This meant the Subaru was better off-road but worse everywhere else, in particular for freeway driving. I never went off road despite living in rural Australia.

I miss the old Falcon station wagons. They were essentially a car designed for regional Australia in every way. They don't make the Falcons in Australia anymore though. Ford insists that a Ford Fusion is the equivalent and imports those instead rather than continuing the Australian production lines.