the real question is, what's it worth to
you? Some people don't want to hassle with shopping out of town, and some are willing to wait for the perfect ride. I've gotten some gems sight unseen, and have been burned too.
Do you plan to work on it yourself, just drive the crap out of it every day, have someone else service it, etc? Will it be parked outside, modified? These are all relevant questions to consider when looking at it. As you know, most cars driven in the winter in Chicago look like that. Is it pretty? no. Is it going to last another 30 years? no. Is it going to fall apart or crumble into a heap in the next 5 years. no. And if it's going to be parked outside, even if you spend the cash on a rust free southern car, it will look just like that one in a few years. LC frames rust- it's just a fact of chemistry. The welds from the factory get ugly pretty quick (unless you live in dry climates). Rust does make working on the undercarriage more difficult. Things break. But Chicago mechanics are used to it. If you're looking for something to keep pristine for 20 years, walk away. If you want something reliable to drive till 2023, it may not be bad.
But back to my original question. What's it worth to you?
If you want to have the bottom cleaned up, plan to spend about 3-4k on remediation of rust and replacing some of those parts. It wont be perfect, but it will help. So if it's otherwise perfect, is it worth 18-19k to you? If not, adjust the price accordingly or pass.
With regular maintenance, rust is really the only thing that can kill the LC other than unintentional intervention like a collision. Just gauge how long you plan to have it in your life vs how long it can continue living
