re: Anyone ever file a Chase Sapphire Reserve trip delay claim?

Yes, got stuck in Orlando back in March because of blizzard in Philly, flight was cancelled. Process is a little involved (had to get all the paperwork, but nothing ridiculous) and after a week or so they sent a request for some additional paperwork, all was paid in a couple of more weeks.

They didn't cover the full cost of the hotel I chose, but that was because I chose a really nice one and could have stayed at a cheaper property.