Why would the owner not spend a few hundred to fix it to make the car worth $1000-1500 more?

$2k is overpriced for a car with issues. My 300SEL was $1k and needed an A/C comp to drive. I took it off the road to rebuild the top end (oil leaks, old rubber was rotted out, etc) and it's a great cruiser.
I've never understood this and that always is a huge red flag for me on vehicles... seems to me there could be else wrong.
If it DOES indeed check out okay, I'd swap a belt while I'm in there, belt tensioner, tensioner shock, maybe a fan clutch, ATF cooler lines, radiator if it's old, inspect the PS pump (they tend to leak with age), the engine switches (aux fan, gauge, CIS sender), and the ignition bits (cap, rotor, plugs, wires) as they're probably due at this point. Same for the rubber under there, I can assure you it's hard and brittle at this point.
This goes along with all the regular services... trans, diff, oil, fuel filter, etc.
Sounds like more than you wanted to hear, but if that stuff is original it's time to be replaced and if you're already in there the time is perfect. It's 18-19 years old now...