One of the golden rules of being a good road warrior who wants to be able to work anywhere is to never, ever, not ever check a bag, especially if you are changing planes.
This is becoming a growing problem and one which only got worse this past week at JFK with American Airlines snafu.
My advice is the same as pal Joe Brancatelli..Ship, Don’t Schlep.
This gives more reasons to working virtually, traveling less and using services like client SightSpeed. There’s no chance of a bag getting lost when you work via a videoconference.