I like the idea of this series being done by various creators who could capture the spirit of their time periods. I'll use the dates for Generations 1 and 2.

1939 by Chuck Dixon and Steve Rude

1949 by Darwyn Cooke

1959 by Mike Allred

1969 by Roy Thomas and Alan Davis

1979 by Roger Stern and George Perez

1989 by Alan Moore and Frank Miller

1999 by Warren Ellis and Jim Lee

1929 (this is actually set in the future) by Grant Morrison & Frank Quitely

I'd buy some of those.
Good luck getting Moore and Miller to work together.

I would imagine not having the publishing rights to any of DC's characters and not nearly enough money to pay anyone would the larger issues, but since this is a "fantasy" thread...

Good idea!

I wonder how Dynamite got the rights to publish the Avengers/Invaders mini.

Alex Ross and money.

The two great comic book levellers.

I'd like any "Generations" set in 1939 to be drawn by Joe Kubert.Having lived during that time,he can evoke the spirit of that time better than anyone else.