I currently drive my 98 Corolla which was bought brand new by my family back then. Its still going strong with 251000 kms on it. Its needed some work, but the work has always been way less than monthly payments of a similar new car. I'm in the same spot torn about what to do next. Its generally needed 600-900$ per year in work. thats been a battery, brakes, both set of shocks, a serpentine belt and pulley, and just recently an ignition lock and a starter.
I'm currently saving up for something newer, although when to bit the bullet is my problem. Its not worth much to sell, but it still runs well and i do my own tire changing, and oil changes on it. so basic maintenance is covered. A lot of any 'issues' with it have been fixed now, so the forecast is looking good. Value wise it would only sell for $1500 low end and maybe $2500 if i really waited and got lucky. I want something bigger with a hatch back, but hate having to consider selling it for that low of a price when i know its been so well taken care of. Everyone else around me has upgraded their vehicles a long time ago and bug me about it lol. Its been 98% reliable so i'm reluctant to sell it even though i would love something newer.