7 bit ascii
Sounds like you've run up against one of the limitations of the computers that the legacy airlines use. That is they use 7 bit ascii which limits the character set they can accept. Enter the name as OLuggage instead of O'Luggage. However, that's about the only latitude you have. Sam was lucky (in my view) being able to travel as Sam instead of Samuel - the TSA and their equivalents round the world can be very picky about things like that and don't get clever about matching document numbers to your advantage.