I bought the Outback Sport after convincing myself this model was worth the extra $2.5k. Could have had the base sedan for under $16k but that just had no appeal, unless you are looking for the lowest price. I still have a 2003 Infiniti FX-35 and it's tough to go from a bull to a lamb. Have to remember this has half the power. Big difference getting on to highway, etc. From the reviews I've read here I would have liked the WRX or STI but I needed to keep the price under $20k. Good compromise between cost and performance. I looked at the CRV and Rav4 but to get the same equip would put you in the mid-20's; also don't believe the new ones are as dependable as they used to be.
Smooth handling and road feel. Overall fit and finish. Outback Sport options: wheels, seat warmers, sound system, steering wheel controls, etc. History of lasting a long time.
Dealer didn't put on the roof rack because he said it would be noisy; not a good design. Get base engine up to 200 HP. Redesign center arm rest. Make bad weather gear standard - floor mats, heated seats, etc. Isn't that why people buy a Subaru?