Mine went out yesterday and is due to arrive in Philly by the end of day tomorrow. I've only had one breakage in shipping beer to comps, and an email was sent to me a week after it arrived at it's destination, i.e. someone knocked it off the counter or something.
I'd be careful with the UPS insurance. If you have to file a claim, they will probably deny it since shipping alcohol privately is against their policy. I'm sure they know what's going on when a ton of boxes get sent to a homebrew shop or brewery, but it would be their out on the claim.