I drive a 2000 Subaru Legacy GT Limited Sedan. I got it with 10k miles on it (pre-mustache) and it now has 99k. It's now 18 years old.
It's been a great car of good quality. I do not use it for work, but do use it for quite a few daytrips, runs to Home Depot for DIY stuff and 2x monthly grocery runs, where I fill it to the brim. I also do quite a bit of hauling, since I do a lot of gardening and a love freecycling. Since it's a sedan -- and the 2000 model eliminated the fold down back seat in favor of a small pass-through -- I have many times regretted that I didn't have a hatchback or wagon. Despite this, I've made it work. For camping, I got a roofbag and hauled stuff up on the roof. For gardening, I put stuff in the passenger seat, with my child's carseat in the back. I have transported a giant picnic table, as well as 6-foot garden benches, a chest of drawers, etc, by putting blanket on the roof and using good ratchet straps. I've become very adept at it. Still, a wagon or hatchback would have been a much better match to my activities now, but 18 years ago, the sedan worked well. I have relatively cheap insurance because of no collision/comprehensive.
Anyway, I am long overdue for a timing belt. It's 110,000 miles OR 10 years, whichever comes first, and the cost is approximately $475. They can and do break, and it's not so much the loss of my car, which is now low value, but it's getting stranded somewhere with a small child. Part of doing the timing belt is often also replacing the water pump, so add that in. My AC stopped working 1.5 years ago and I didn't fix it. Pretty sure I need back brakes and new rotors all around as well (rotors needed doing before and I deferred). And most of these cars end up with head gasket issues that need to be addressed at some point, although mine has not yet.
I think reasonably, without repairing the AC, that it's time to put somewhere between $500-$1,200 into this car, without fixing the A/C. While the mileage is low for a car this age, the inside has some damage from my hauling activities, so I don't expect the value is much.
I'm contemplating putting that same money into another car that better suits my lifestyle. The Subaru Outback would be perfect, except I'm not thrilled with Subaru gas mileage. Love everything else about them. I'm talking a good used car, that has already had the timing belt done, that has working a/c, with breaks/tires/rotors in good condition, etc. On the other hand, the devil you know....I've had this car the whole time and know how it has been treated. And on the third hand, it really regret not having a hatchback or sedan and could switch at this point.
A couple of points: I'd only pay cash if I got something else, and I'm thinking around 5k would be my budget, but at that price I'm looking at something with probably more miles than I have now. I am in a metropolitan area, so do not have storage for a trailer. I could add a roof rack to my current car, but that's around $300 and a hitch and cargo basket would add another $600 (and the cargo basket would have to stay on full time since I've no garage or place to store it).
Thoughts?