Great post! When you think she was born in a world before the invention of aeroplanes and with telecommunications in their infancy, using Skype is an achievement indeed!
"6) I'd say my chances of at least reaching 100+ are quite good too based on heredity and genetics." - make sure you're not hit crossing the road tomorrow now after saying that...
"I should expect to reach the next century. (I'm currently born May 2001, age 16) " - pity you weren't born a few years earlier so you'd have a chance of spanning 19xx to 21xx. Awesome that you are exactly 100 years younger than Great Aunt Chiyo though and that she lived past the 100th anniversary of that photo!
"... covered the assassination of the Russian Royal family in 1918 (which she believed to have been the most important event to have occurred in her life)."
- No wonder. The Russo-Japanese War would have been one of the defining events of her early childhood.
" ... to avoid the hardships of WW2 (she did not agree with the Japanese regime at all)" - What was her reaction when she heard about Hiroshima and Nagasaki?
I'll just throw out some basic questions you can ask her:
1. What is the biggest technological change she has seen? (Aeroplane, telephone, television, refrigerator, penicillin, internet, etc)?
2. What is the biggest cultural change she has seen? (Let's remember Japan is a VERY different place now than it was before the war). Is it too materalistic/Americanised for her?
3. Does Abe worry her? Is Japan going back a little in a more martial "1940s" direction?
4. What was her favourite decade to live through?
5. Are people becoming more or less civilised or is human nature basically staying the same?
6. What would the people she knew as a child think of the world today if they were still around? Good points, bad points?
7. Which famous person has had the biggest impact on her life?
8. What are her favourite improvements to the way people live over the last 100 years?
9. What changes does she like the least?
That'll do. There are thousands more questions I could ask but I will restrain myself...