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As for Puerto Rico, I checked the 1956 and 1960 elections (before and after Alaska and Hawaii became states) and then the 1964 election (after DC was allowed to start voting). The two incoming states added 6 electoral votes by 1960 before the census was accounted for. by 1964 and the new census numbers (plus DC would get 3 votes) they had the population to add one more electoral vote and redistributed from there (Hawaii gained one more from 1960 to 1964 and someones else lost 3 to go to the District of Columbia). It was 1964 were we got 538 electoral votes as we have now.
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