I'm looking at a few 97-99 Outbacks to get as my winter vehicle. They are beautiful wagons and if I like the Outback, I may get a new Impreza in the Spring!
The ones I am looking at are high mileage, 275-300+ km (170K+ miles). One has a replacement engine with 65K km (40K miles) on it and 330K km (205K miles) on the body, new battery, and fully loaded. The other has 287K km (178K miles) on the body with an almost new transmission with 60K km/37K miles on it, fully loaded but will need a brake jobs and will sell with black steelies.
I have read that brakes and wheel-well rust are common issues amongst the Outbacks, but is there anything else, particular to the Outback, that I should look for when I inspect and test the used prospects?