The Benz C280 is 33k, the Audi A4 with the v-6 starts at 34k. The only thing I see that the Audi has over the 9-5 is 4wd, and they seem to adressing that in the next few years.
Audi reliablity is garbage, and benz is no better. My father used to drive an E500 that was in the shop so much with brake and electrical issues that under the Minnesota lemon law, he got to return it.
Ask a quattro owner (or any Audi owner) about c/v joints, or the four catalytic converters the cars have, or the electronic issues, and then run away.
As for the "dated" comment, what other cars are you comparing it to?