My sister has a 2000 outback with 160,000 miles on it. No headgasket issue as of yet. My mom just got a 2005 with 140,000 miles and supposedly the head gasket was changed when a new timing belt was installed. My dad and I both have first generation Legacy sedans with I believe the 2.3? (I just got mine so not to familiar with it) with almost 300K each and the only gaskets that are bad on both cars are the valve cover gaskets. Dads car has been driven very hard, mine was my moms prior to me purchasing it from her, and was driven light for the last 100,000 or so miles.
Can't speak for the head gasket issue, as I have never been much of an import car person. I do remember dad working on my sisters outback once, having had the motor torn apart, but what he was doing I am not sure (we share a 2 car shop, and at the time was rebuilding my Ranger whilst he was working on the Suby). But, knowing the family are Subaru freaks tells me that minimal problems will be had, so I am pretty happy with that.