After digging into this a little more, I think the booklet with Constante on the cover has to be 1952 and the other one a Bacardi promo version from the mid to late 1950s, as discussed.
The chief determining factor for the first one is the presence of the “Mr. John Ringling North” highball on p. 50. North was the director of the Ringling Bros Barnum & Bailey Circus, which beginning in December, 1949, began making yearly visits to Cuba. However, as this January, 1952 bit from Robert Sylvester’s “Dream Street Beat” column in the New York Daily News (January 20, sec. 2 p. 7) suggests, the dcrink most likely dates from 1952:
The Vat 69 ad mentioned above adds the not later than 1952 limit, more or less: George VI died in February, 1952; by April, anyway, Vat 69 was replacing this logo, as found in the Floridita booklet:
with This one:
Even allowing a little time for things to reach Cuba, that doesn’t put the date of the booklet much past late 1952.
The other booklet is more difficult. All we can say is that it is after the 1952 one. It removes all of the names of the dedicatees from the drinks found in the 1952 one (and previous versions), and almost all of the drinks named after Cubans (some 14 drinks). In return, it adds seven simple Bacardi drinks, amost all of them Bacardi versions of classics such as the Alexander, the Manhattan and the Julep. Perhaps they would have had to get permission to use people’s names in a promotional booklet.
Anyway, that’s my best shot at this rather thorny problem.