Depends on how easily they pull and if you can feed them without kinking. Your problem probably won't be the pull but wrestling with 40 boxes. I always opted for cable on reels. Definitely two men, maybe three depending on how long. Might want to do two pulls of 20. Also, plenum kinks just looking at it.
Keep in mind also that 40,000 feet of cable is big bucks especially if you are only pulling a hundred feet. So it pays to buy 10 boxes and do four pulls.
Use ten boxes and with each pull have a pull string to use on the next pull. Yep a three person job, one on the boxes, one at the entry to the tray and one pulling. I have never used spools for Cat wire but not a bad idea, set up on an axle
Our crews use boxed cable, up to 10 individual boxes depending upon the total number of cables. It's either 2 people or 3 people, again depending upon the number of cables, total length of the pull and other conditions. Don't apply too much stress to the cables as the individual conductors are on the order of 24 or 22 AWG.
There are two types of "boxed cable". There is the reel-in-a box and "Unreel" where the cable is wound like a ball of twine using no reel.
Reel-in-a box cable can be hard to pull, especially when you have multiple boxes. But the advantage is that you can take the reels out of the boxes and pull off a wire cart if you have multiple runs. It's the way to go when you just need to pull single runs.
Unreel I have no patience for. Inevitably some boxes will get tangles inside making you stop and cut open the box to try and fix it. I drop kicked one box across a space once because it kept happening during a 100 foot pull.