I have an update...um, just because.
I visited Gallo-Miller, the shop doing the work on our Outback, to see their progress. Dave Miller was very accommodating and showed me the work they had done and what they had found since we dropped it off almost two weeks ago. All they had really done so far could be described as 'exploratory.' None of the sheet metal had actually been removed yet. The inner right quarter panel and right B-pillar both have to be replaced, so the estimate tops ten grand now. I imagine that there are few surprises left to find, so I doubt it'll hit the magical 75% get-a-new-car mark.
They're waiting on some of those parts, so I don't think there's a chance the car will be done when they originally estimated.