One way or another, you NEED to look under the hood before making a decision. Rust in general is probably the #1 killer of Caddys, and specifically strut-tower rust. If the strut towers are chewed up really bad (usually is worst at the base) then walk away unless you're willing to weld in new metal; repairing that area usually involves taking clean strut towers from a donor car and welding them in.
Also look for bad rust around the windshield and back window, not impossible to repair but it can be a real PITA.
$2000 is a bit pricey if you're going to do a complete teardown anyway, I would definitely try to get him lower, especially for a truck with some moderate rust issues.
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