The Outback was our first "new" car, and we can certainly afford anything. This car has been completely troublefree, aside from the cupholder in the back seat that my kids stepped on (and broke). There is a lingering concern regarding head gaskets with the 2.5 engine. We have had no trouble at all. I do not know what incidence exists for these engines. We have a Subaru fanatic nearby who will change both sides for about $1500. Would I buy again? You bet - in fact, we're shopping right now for a Forester for her, so that I can start driving the '01 Outback - my '91 Loyale has 209k on it, and running fine but a bit of an embarrassment in this neighborhood.
Still some work to do on the "hillholder", but it's a minor irritation.