We bought a new 2017 Outback last fall. It was the base model with a manual transmission (not available in the U.S. - we are in Canada). Unfortunately, this was at a time when there were no rebates, but we needed a new car after our old one completely died suddenly. We ended up paying the sticker price, but they provided us with a rental for three weeks until our car got in.
The choice was between an Outback at more or less sticker price or a $5,000 discount on a Pathfinder. Ultimately, the Outback won out, largely due to my wife's lobbying. It was the closest thing we could get to our manual-transmission AWD Passat wagon that had died.
I have noticed for years that when buying a base model car, it is better to just buy new. $5,000-$7,000 off a car with 70,000 km just isn't a good value proposition to me. That represents about seven years of driving in our household.
I was aware of (and am scared of) the head-gasket issue down the road, but otherwise the Subie is a "goldilocks" car. The ground-clearance is just right for snow-covered back lanes (which don't always get plowed in our city), the wheels are the right size to traverse most pot-holes and railroad crossings without damaging the rims (we have bad roads in our city), the roof rack is a neat design good for hauling bikes and Christmas trees, the kids have enough space, and with a trailer hitch I can pull a utility trailer when I need more space. And it still fits into our "compact car" spot in the underground parking garage at our condo without annoying the neighbours. The only downside it that it doesn't drive nearly as nicely as our 13-year old Passat did. It took me some time to get used to the very soft suspension.
All in all, I found the car to be a good value proposition. With taxes, fees etc. we paid a bit over $34,000 Canadian. To me, that is not unreasonable for a fairly large family car with all-wheel drive.
Leaving aside reliability issues (to which I cannot speak because the car is too new), I find that Outbacks are the Volvo 740s of the 21st century - spacious reasonably rugged wagons without oversized engines or too much technology.