I think it would have been ideal to have been born around 1930 resulting in being about 15 at the end of world war II. From there I would have been ahead of the population bubble of boomers and enjoy a life of buying cheap housing, real estate, and most types of investing, always being ahead of the wave of boomers needs driving prices up.

I would have been old enough to have been an adult during the 50's and 60's to have enjoyed the golden era of western mule deer hunting, as well as the horse power race of OHV V-8 engine cars, and
fast and easy women from the era after the pill but before aids.

If a guy was born in 1930 and still alive today, he would be 90. Old enough to enjoy his grand children growing up and starting their older families before leaving behind the world and technology.