IGX

A "guy I know" left his iPad on an airplane in Chicago. He put it in lost mode.

Should he wipe everything like Hillary Clinton or hope the airline comes through for him?

Airlines are good at getting these back to you if you alert them quickly. If it's clear they can't, remote wipe it, buy a refurb, and restore from backup.

http://www.dailymail.co.uk/travel/trave ... lfies.html

You could get it back. Stranger things have happened.
My mother left one on an American flight last year and it was returned without crew selfies.