I bought my Outback Sport with 70k miles. I'm at about 125k now, and besides routine maintenance, the car has not cost me anything. This is exactly why I bought the car. I know that Subaru has addressed in the new OS/WRX all of the issues I had with this one (hp, wheels, etc.). That being said, I realize this car is a '99, and for what it is, I'm totally satisfied. If you don't abuse the car, you won't have any problems. Mileage is decent (mid- 20s). Interior room? I'm a drummer, and I fit my entire kit, plus a passenger! AWD? Put a set of snow tires on in the winter, and the car is unstoppable! Finally, get a set of WRX style wheels for the car, and improve the looks 100%.
Versatility; interior room great for small car size; small exterior size great for city driving/parking; capable in ANY weather; ABS.
HP, wheels, cup holders (all of which Subaru has already addressed).