I’m reminded of that old question. If you could have dinner with anyone, living or dead, who would you choose? If you are privileged, most of the recent historical figures would accept your invitation. If the person you chose was infamous, like Hitler, you’d ask him questions, like “how could you do that to those other people?”
The invitations of less privileged people might be rejected altogether if the historical figure was homophobic, sexist, or racist. If you are less privileged, you might ask, “why did you do that to my people?”
And I’m not talking about someone with ancestors from England inviting a viking to dinner and and saying, “you probably did something bad to one of my ancestors.” I’m talking about recent history.
Further, I recognize there are people with a family member at Pearl Harbor who could yell at a Japanese general, but that was a politically motivated atrocity aimed at a military target (though many civilians were killed). It’s not quite the same in my mind.
It’s said that privilege is almost invisible to the privileged themselves. I hope this hypothetical situation can help people start thinking or talking about it.
The Phoenix Series 
Black Like Me sounds like a fascinating book. I’ll have to pinpoint the views of both and their biases and you make a good point that the longer someone lives the more experiences they have and the longer they’ve had to examine them. Provided they become aware of them.
The point about military solutions is great as well. I’ve noticed he does understand the diversity of the armed forces the strengths and weaknesses of military solutions. Sometimes people who are deep inside a culture, don’t know what it’s like within any other.
Being in the military *can* widen a person’s self-understanding. Occupation forces have contact with cultures in the occupied area, for example. I’m thinking of American occupation in Europe after World War II, as well as our current Iraqi presence.
Further, serving with other soldiers from different areas is experience that a homebody wouldn’t get, especially in pre-industrial societies. Here, I’m thinking of the Holy Roman Empire, which was multi-ethnic, and which would use mercenary forces from multiple different regions in joint operations. These combined forces had their own internal conflicts, as you’d expect, but they did operate together.
My point is that military experience does have boundaries, and military forces are used only in specific circumstances. A soldier has to obey his chain of command, and he can’t roam around freely to gain a broad set of life experiences. So, his personal life choices have to be compatible with his superior officers and the engagements of his service, or he’ll be removed from service.
I’ve noticed that the soldiers I’ve worked with over the years will sometimes develop a thoughtful attitude towards their service that is, somehow, compatible with remaining in service. Long-time noncoms, elite forces, and officers making promotion during conflicts seem to be those that are most likely to think deeply about their involvement. Famous examples include General Omar Bradley and General Douglas MacArthur.
Your 251-year-old Marine has the advantage that he dies and comes back to life. That’s the ultimate separation from service! This means that he could have many experiences gained from his lives between enlistments.
Getting back to Black Like Me: After my previous comment, I was prompted to look at what else the author did. There’s a couple of other related books that look interesting (that I haven’t read yet). First, there’s the biography by Robert Bonazzi, Man in the Mirror: John Howard Griffin and the Story of Black Like Me, and there’s the author’s later work, Prison of Culture: Beyond Black Like Me. Those could well be worth reading.
Have you read the 1961 book, Black Like Me, by journalist John Howard Griffin?
It’s the true story of the author, a white upper-middle-class Catholic Texan man who, in 1959, used methoxsalen and UVA treatments to turn his skin dark brown. Then, after shaving his head to disguise his straight hair, he traveled as a black man through the segregated American south of that era to document the experiences of black people which were invisible to whites.
It’s illuminating in many ways. On the one hand, it describes his increasing realizations, starting at age 15, of his own privileges of race, economic status, religion, region, and gender. At the same time, reading between the lines, one can see how he continued to be unconscious of aspects of his privilege, even during and after his experiences as a black man.
John Howard Griffin died at age 60. He began to understand his privilege at age 15. That 45-year difference was enough for him to gain significant self-understanding.
So, your Marine character, with an additional 191 years of life, has had enough years to have understood his privilege, but did he have the life experiences to start thinking about it? Your Alaskan Native character probably also has the years, but how about the experiences?
Since the Marine chose the military life for a significant part of his 251-year life-so-far, he accepts military solutions. That’s an area where his life experience has been limited, and may yield unconscious biases towards his own privileges. Similarly, what life choices made by your Alaskan Native character limit his/her self-understanding?