My first question is "How do you define someone who is 'living free'?"
Or even "What do you mean by 'free'?"
Do you mean living "free" politically? Should I imagine Mel Gibson's William Wallace yelling "Freedom!"
Do you mean living free from fear and anxiety?
I'm assuming New Hampshirites would mean living free from the rule of a king. So, context is important so we don't impose meaning on top of theirs (for the moment!): 3:8 State Motto. – The words "Live Free or Die," written by General John Stark, July 31, 1809, shall be the official motto of the state. Source. 1945, 152:1, eff. May 10, 1945. So it became their motto in 1945 in the context, no doubt, of World War II.
The General John Stark in question penned what would become the motto as the postcript to a letter:
I find it very interesting that Stark included "death is not the greatest of evils." As we know, death is nothing to us. I'll consider the Epicurean implications of this later. For now, that seems to me a fascinating little context for a deceptively simple motto.