The next group of Tri-points in the collection are along the lines that are pictured in The Catalogue, and what you would "normally" see when you find one:
Note the flat ball clips with hyphenated "Tri-Point" lettering:
and the larger buttons:
But that one on the right is made from a distinctive celluloid which resembles the later "Chicago" Conklins:
OK, it doesnt "resemble" it, it's exactly the same:
The use of a Chicago Conklin celluloid provides another silent clue as to when these were made. Conklin, the venerable manufacturer from Toledo, Ohio, barely survived the Depression and was sold to a group of investors in 1938, who moved the company to Chicago. Quality quickly deteriorated, and what was left of Conklin -- by that point pretty much just a name -- was sold to the Starr Pen Company in 1941.
The Conklin pencil pictured was made during the Chicago years, before the acquisition of Conklin by Starr (we know this because Starr-produced Conklins were the same as Starr's other inferior brands, except for a different name on the clip). It's possible that Nichols bought up some leftover celluloid after the company was sold to Starr, and it's also possible that whatever company supplied Conklin with its celluloid was simultaneously selling it to other companies.
Either way, I am confident that the existence of a Tri-Point in this celluloid is a pretty good indicator that the ball clip was abandoned long before 1944, even though the 1944 patent application for Nichols' improved version of the Tri-Point shows a small ball clip.