Born in 1910 +/- with enough money to be fed and avoid disease. Put my family $ in the right places and make money off the stock market crash. Maybe do a hitch in the Corps during the crash to get some Banana Republic fighting and weapon experience and see the world.
Be in my 20's in the '30's to travel the earth and have adventures. Modern civ and medicine in Western enclaves but still a whole lot of "red in tooth and claw" world to test oneself in.
The aforementioned development of Jazz and Swing (flirt that skirt baby), good lookin' suits, hats, smoke's not bad for you (
) full auto's in stores....
Reenlist as an officer and fight the Japs in the Pacific, pick up a Navy Cross along the way.
Move to LA on the way home, marry a budding pneumatic starlet and build a real estate and water empire.
Die in bed surrounded by grandchildren sometime this decade.
Good times....