No, that's never happened to me (thank goodness). If I remember the fine print on those little laundry slips, though, I think their liability is limited to some ridiculously low amount like ten times the amount the charge to clean an item.

And I know this won't make you feel any better, but why did you send a $500 sportcoat out via the hotel cleaners, the day before checkout, when you needed it for meetings the next day? Unless somebody spilled a glass of red wine on you, it just seems like an unnecessary risk (that in this case, unfortunately, was realized).

All that being said, I'm still hoping the hotel does the right thing. Either by finding and returning your cleaned coat or by reimbursing you without lots of grumbling and delay. Any chance you can find out what cleaning service they use and try to deal with them directly?