wbp2 - Your tractor is a mid-1942 year of production, and seeing as it has Olive Drab as its primary colour, it would almost certainly have been part of an early 1942 military purchase order .. a period when military purchase order numbers practically doubled monthly.
I seem to recall that all Cats coming off the production line were still being painted yellow for civilian use, and OD for military use, in mid-1942. I think it was late 1942, or early 1943, before all Cats came off the line, in OD only.
Once civilian purchase restrictions came into place, around early 1942, it was difficult for civilians to purchase tractors unless they could prove a critical need, or were engaged in vital war production work.
One of the first of a number of the "limitation orders" of the War Production Board, was a directive, on 19th Feb 1942 .. which prohibited the sale and delivery of track-laying tractors to individuals and organisations who had a preference rating below A-2.
Steel was in short supply in America in 1942. Until more steel plants could be put into production, even Caterpillar was on rations. For July of 1942, Cat ordered over 72,000 tons of steel, and received a little over 47,000 tons. D8 production was down 36% on projected production. It was a tough time to be a civilian looking for a new tractor.
The figures in the publication "Yellow Steel" quote that from early 1942, the military was taking 85% of Caterpillar tractors produced, and the remaining 15% were allocated to contractors for high priority war construction projects, or agricultural producers that were producing food for the military forces.
It was noted that from mid 1942 to late 1944, Caterpillar dealers had virtually no new tractors or Cat equipment to sell, due to the overwhelming demands of the military. The dealers survived by overhauling old tractors, and salvaging and reconditioning parts, that were previously considered to be good only for scrap.
There were only 342, 8R's produced in 1941 .. meaning that approximately 9650, 8R's were produced between Jan 1942 and early Dec 1945. The 2U series appeared in late Dec 1945.
Approximately 2500, 8R's were produced in 1945 .. but military tractor orders slowed appreciably in late 1944, and ceased abruptly in early August 1945.
On that basis, it wouldn't be unreasonable to assume that around 80% of the 8R's produced between Jan 1942 and Aug 1945 (approximately 8650 tractors) were military tractors .. making the total number of military 8R's probably a little under 7000 tractors.