I have an '01 Outback - bought it in fall of '01 with 9k on it, had been a rental. Currently has 95k miles on it and has been my wife's daily driver since we bought it.
This ended up getting pretty long, sorry, but I've been doing a cost/benefit analysis of keeping it a few more years in my head, was helpful for me to put it all down on 'paper'.
Here's a complete list of the problems I've experienced in 9 years of ownership, and the costs to rectify:
Front rotors are undersized. Replaced mine with some upgraded drilled and slotted ones, not only do I look cool but it stops better and no more warping issues.
Cost: $400 including pads and labor
Lightbulb in the PRNDL stick burned out at about 30k miles.
Cost: $1.25 and 30 minutes.
Big plastic piece across rear tailgate prone to leaking in heavy rain.
Cost: Some RTV and a couple hours of my time.
Factory alarm failed. Needed a whole new control module, which would have been $800 some dollars, but it was right at the 36k warranty so we got a new one for free. It has failed again - but I'm thinking I'm just going to get a cheap remote entry system installed. We don't need an alarm where we go anyway, but it's nice to be able to unlock the doors remotely when your arms are full.
Occasional fuel smell in sub-zero temps caused by fuel supply lines contracting in extreme cold.
Cost: Once we figured out the issue - once every 2 years I need to spend 10 minutes in the engine bay with a phillips screwdriver tightening the connections.
OEM engine skid plate is plastic. Found that out in '06 when we had 12" ice ruts in our culdesac for 3 months.
Cost: $180 for an all aluminum STI rally skid plate and an hour on my back in the snow (didn't want to take any chances with an aluminum block and all that deep snow around).
Cabin gets really hot in the summer (black interior, lots of windows)
Cost: $250 for a professional tint job.
Goes through tires pretty quickly.
Cost: Buy tires at Discount Tire, they are happy to rotate and balance any time you want. I go in early on Saturdays, they often don't even bother to check if it's been 6k miles since the last time they just run it into a bay and rotate and rebalance the tires while me and the counter guys talk about trucks and drink coffee. Might help that during the last 10 years I've bought tires for a Taco, an FJ40, an FJ62, a 4runner and the suby there.
Wind noise at highway speeds. Its an inherent defect in this vintage Outback, not sure about other years. Luckily Subaru installed a wind noise cancellation button on the dash - they labeled it 'volume'

Its right under my other favorite factory installed feature, the weather band radio. My kids go nuts cuz I like to "listen to the robot" when we're on road trips.
Currently dripping oil from the rear of the block. Several possible causes, will be taking it into the shop for a diagnosis next week, when it needs an oil change anyway.
Cost: ??
The paint on the hood is developing this weird 'star' pattern. I don't know how else to explain it, small star like lines in the paint, each about the size of a penny. I wouldn't be surprised if it was in an unreported front end accident and Hertz did a poorly prepped respray of the front end, but it's not rusting or peeling and it drives straight. Has been happening for 4 or 5 years.
So while I'm bummed about the oil leak, and somewhat nervous about the head gaskets, although we've had no problems there, when I add it all up the cost of ownership has been pretty small for 9 years of daily driving.
On the benefit side - phenomenal in the snow. I would drive this car anywhere, anytime, with the 'all season' Pirellis it's got on it with no hesitation. Like all cars it has its quirks - if you're playing around and you let the back end get away from you, the back end is going to be driving the train pretty quickly. I imagine the newer VDC versions don't have this issue, and its really only an issue when I make it an issue.
Comfortable. I'm 6', 200 lbs and I can easily handle 15 hour days behind the wheel. One of our favorite family trips is the non-stop Boulder-Tucson jaunt to visit the grandparents. 969 miles, 15 hours.
The passenger seat could use some more adjustability. If I could lower it I could be a happy passenger too, but honestly I'm never happy as a passenger so I like having the excuse of always having to drive.
Reasonable economy. With 2 adults, 2 kids, a 60lb dog and a Thule box on the roof it gets 26mpg on the highway at 70mph. That drops to about 24 if you push it up to 80. Will easily cruise on I80 from Laramie to SLC with the cruise control set at 92mph, or so I've heard :smiley_drive: but mpg dropped to around 23. Around town is not as good, with winter fuel we often see it dip as low as 20mpg, but it mostly drives around town, lots of stop and go, etc....
I've never had a headlight or foglight burn out. I see them around town with burned out lights constantly, but it has never happened to me.
So when I add it all up, (and I hope this was as useful for you as it was for me as I decide what to do) the cost of ownership over the last 9 years has been very small. I've said it before, but if I knew how much I was going to love this car when I bought it, I would have held out for a 5 speed, just to make driving more engaging.
After this quick analysis, I'm thinking about getting the oil leak fixed, and then banking $250 a month as a hedge fund against possible head gasket failure. I haven't had a car payment in 5 years and I'm not in any hurry to have one again, and I could happily drive this car for another 4 or 5 years.
It's already driven the family all over the place (winter time drives to Jackson Hole, Telluride, Steamboat, Vail, Tucson) and we have a long one planned for the summer - several states.
Luckily we have SuperRupair here in town, it's the Subaru equivalent of what Slee is to the FJ80 crowd - so it's in good hands, mechanically. Final analysis - no regrets about my Suby and would happily buy another one.
-Matt