I'll start this off simply: I think of Jeeves as 10 years older than Bertie (although I know there's no official answer). Born in 1890 and 1900 if I want Bertie to be in his mid-20s during mid-Prohibition. Maybe 1900 and 1910 if I want them to be alive and kicking in the 70s and 80s.
Re: J&W headcanons