I guess I'll chime in here. Although I own an Impreza 2.5i wagon I feel I can comment about other aspects of the vehicle that are often overlooked or looked at as a general consensus (ie: 5 speed vs auto). As far as the engine goes, I bought the vehicle with 62k miles on the clock and the owner was nice enough to throw in a free oil leak. I smelled oil but did not see any drops when I bought the vehicle, and he showed me a receipt from the day before stating that the car received an oil change. No big deal sometimes theres a little spillage when doing an oil change and I thought to myself that it will go away. Long story short, it didn't and it ended up being a cracked oil pressure switch. This cost me a new head and around $1800 at the end of the day for what I thought was a little burnoff. It seems as though these switches only require the slightest amount of torque to get them snug and since the head is aluminum, and the switch is iron, you need to be very careful about how you approach this. I got that fixed and was a happy camper, and then my CEL came on informing me that I had a clogged cat. Well I have 76k miles on the clock now and federal law mandates that the manufacturer replace the cat is it is malfunctioning under 80k miles. I lucked out there and just had that done last week.
As far as the Transmission choice goes, I would highly recommend driving both to get a feel for what you like, and will tell you that the throttle by wire is difficult to get used to on the cars in my opinion. My prior vehicle was a Miata whose transmission was almost telepathic. The accuracy and immediacy with which the car shifted was one of my favorite aspects of that car. When I went to the Subaru however, it seems as though there's a delay from the point in which you step on the throttle, and when the engine revs, and it never seems consistent. I find myself over revving, under revving, and when I first got the car stalling out. There have been similar reports about this that you can look up on more Subaru specific forums. Once up to speed though everything seems to work out. Although the car is rated for 22/ 29 mpg, I find myself getting in the upper 20's in the city and have achieved as high as 35 on the highway, flat stretch of highway to beach. I've tested the all wheel drive on this car on Carova Beach, NC which has some pretty powdery sand, in the snow, mud, and gravel, and it has far exceeded my expectations. Ground clearance was an issue on the beach but as long as I kept momentum I was good, which shouldn't be as big an issue with either vehicle you describe. As with the Outback and Forester you have to keep in mind that these cars were not built military specs, but will be more than enough should you be traveling down a dirt road and find a mud puddle a bit larger than you expected, or a snow drift that needs a bit of convincing.
Despite what looks like a horror story at the beginning I really do enjoy having my car and am happy with my decision overall. My budget was also $10k and from what I found 05-09 Outbacks are going to have pretty high miles for that price. The older generation might be a consideration, but at the end of the day you have to drive the vehicle and see what works best. Gas mileage was pretty high on my list which is why I stayed away from the turbo or 6 cylinder varieties. One gripe I have, or I should say my backseat occupants, have about my car is the lack of legroom. I know the Forester rides on the same platform as the Impreza, but it may be a different story given the bigger body. Just something to consider since the Outback is a bit longer. I hope I helped out.