A quick spotlight on Tedesco, and I'm hoping Brad Tufts chimes in with any information to add to what is included below.
The club was organized in 1900 with a 6 hole course (quickly expanded to 9), with a new 9 holer built in 1902/03 at a new site.
1901 Harpers Official Golf Guide -
1902 Official Golf Guide -
May 1903 Golf Magazine -
Sept. 1903 Golf Magazine -
Ross shows up in 1912 (as noted earlier in the thread) and adds 9 new holes and reworks the existing 9.
Feb. 1912 American Golfer -
July 8, 1912 Christian Science Monitor -
Around 1926 the club decided to expand to 36 holes.
Jan. 1926 Golf Illustrated -
May 1926 Golf Illustrated -
I don't have information on who completed the first 9 additional holes. The second 9 appears to have been a joint effort between Ross and Wayne Stiles, although the later two articles suggest Stiles was primarily responsible for the work along with club member Eugene Clapp.
Jan. 17, 1929 Boston Globe -
June 20, 1930 Boston Globe -
Feb. 7, 1931 Boston Globe -
In 1932 Tedesco's clubhouse burned down (leading to some of the confusion over its architectural history). The following article notes Ross offering a few suggestions on the course at this time, with my guess being this work was on what was considered the 18 hole 6,400 yard championship course at that time.
April 4, 1932 Boston Globe -
By 1934 the club was still tinkering with the layout and adding new holes. The account below gives credit for the course to Ross, but I would guess several of the holes used were part of the addition made by Stiles.
April 6, 1934 Boston Globe -
What is left is a bit of a mystery. We know Ross was wholly responsible for at least 9 holes of the 36 holes that would be built, with Stiles most like responsible for at least 9 of the others. It is possible that the two men collaborated on the last 9 holes built. The story that Skip Wogan rearranged the course in the mid-1930's seem erroneous, as that work apparently was done pursuant to the suggestions of Ross. Brad has also indicated that Ross left notes with the club around 1937 for additional work.
The biggest part of the mystery for me is trying to decipher what holes ended up comprising the course that exists today, what holes were abandoned and what holes ended up as the "Gun Club Nine" and spun off as the public Sunbeam Golf Course. There are clues in the descriptions of the locations of the new holes carved through the rock strewn forest area that was developed in the late 1920's, as well as the description of holes located on the "bluff side" of the property. Hopefully Brad has a good deal more information on this front.