A few questions that might help narrow down some dates.
1. When exactly did Marion Hollins move to California and take up her role with Del Monte (in 1922 she was occupied with the construction of Women's National at Glen Head)?
2. Was Cypress truly her idea, or was the idea of the course already in play before she joined Morse's concern?
3. When did Charles Cheney start working on plans for the residential layout of the Monterey Peninsula?
4. What does the unmarked version of the 1921 Map look like.
As an aside, one of the more heralded books on MacKenzie notes the following:
"The real impetus for Dr. MacKenzie's trip to America in 1926 was Robert Hunter's interest in the land that would become Cypress Point Club."
Seeing as MacKenzie departed for the US on Jan. 13, 1926, and Seth Raynor was still alive and by all accounts still the architect of record for Cypress Point, I don't see how the above statement holds any water. The tragic loss of Raynor at the early age of 51 must have been a blow to Hollins and the rest of the founders of the club. The fortuitous arrival of MacKenzie in California right at that time almost strikes one as divine intervention, but it seems inconceivable that Cypress was in any way on MacKenzie's radar when he embarked for these shores.
One lingering question I have on the transition from Raynor to MacKenzie/Hunter is who would have built the course if Raynor had survived? From a timing perspective, we know Raynor had planned the Dunes course at MPCC and construction was underway as early as the Fall of 1925. I don't know who Raynor had on the ground at the Dunes course, but I suspect the same team would have continued the work on the Shores course and at Cypress.
Sven