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- At what point did his duties related to the Spanish-American War begin? Did he volunteer to join the fighting, or was he part of the regular troops?
- Where was he stationed during the war? What were the people and the surrounding areas like? How long was he there?
- How did he keep in touch with his friends and family back home during this time? Did he save any letters he might have written or received?
- Did he become close friends with any of those he served with? Did they keep in touch in later years? Did he save any of their lives? Did they save his?
- What were his duties? Did he participate in the fighting? Did he have medical or transport duties? Was he especially skilled at one particular task?
- What was his most vivid memory of this time? Specific people or places? A certain event?
- Was he injured in any way? Describe what happened. What went through his mind when he realized he was hurt?
- If he was injured, did he heal quickly or not? Did he return home because of the injury, or did he go back to fight? How did his injury change him in ways that he noticed years later?
- Did he ever need to take someone's life? Describe the experience and how it affected him both immediately and in the long term.
- In the end, Spain gave up Cuba, the Philippines, Puerto Rico and Guam. Did he leave the service after the fighting was over? Did he feel that his efforts had served a purpose?
- If he had volunteered to fight in the war, did it turn out to be exactly as he had expected? Was he able to return to "normal functioning" afterwards, or did it have an emotional impact on him?
- After all was said and done, what did he learn from his experiences in the military? Why were these lessons valuable to him? How did they change him and his ideas or values?
- How would he be different if he had never had these experiences?
- What sort of memorabilia did he save from this time? What did it symbolize to him? What memories and feelings did it bring back after the war?