I'm surprised this is so triggery to people.
My grandparents were born in the great depression. Eventually... they were very successful, traveled extensively for business and pleasure, and NEVER booked what they wanted. My grandmother always asked for an upgrade (airports, hotels, restaurants, etc). She often got one.
When I read these kinds of arguments, I feel like the people who come from money are horrified and the people who didn't come from money are not. Meh....Ask for an upgrade. THE WORST thing that can happen is the person you are talking to things you are a looser. Who cares if they think you are a looser? You NEVER have to see them again.