From the nature of the plant, the many descriptions (here and elsewhere) invoking Wichuraiana, and the number of references cataloguing it or explicitly stating it to be a Wichuraiana hybrid, I think the "Sport of 'Red Letter Day'" parentage should be abandoned. For just two examples: Kordes 1935 has it as a Wichuraiana; 1931 Gardeners Chronicle mentions it as "a valuable and striking Hybrid Wichuraiana" (p. 38). Chaplin's indeed was producing Ramblers and Large-Flowered Climber hybrids in this era.
From the references it appears that ‘Crimson Conquest’ may bloom just once a year (albiet for a long period). I am guessing at the same late time as ‘Excelsa’ and ‘Dorothy Perkins’. At the moment HelpMefind has “Blooms in flushes throughout the season”. Can anyone confirm the flowering season?