Hi Mark, what I meant was removing the bearing cages from the transmission housing, not removing the bearing cups from the cage - that's easy once you have the cage out. You can shrink them - I sliced mine as I'm a dab hand at slicing stuff with a gas axe but whatever you're comfortable with. You could even put a couple of 1/4" holes in the cage to drive the cup out with a punch if I'm remembering it right. The suggestion for putting a hole in the shims where the forcing screw bears is to avoid the possibility of messing up the shims. to be clear, the forcing screw suggestion is to remove the cage from the housing (you're calling the cage a cover). A couple of holes won't affect the shim's role in spacing the cage out from the housing. The cup is in the cage, and the cone is on the shaft. I also had to slice the cone off the shaft as I couldn't get a puller behind it, not even a bearing cone puller. Of course, : ), your cages might just pull out easily by hand. Mine were tight in there but yours might not be and it sounds like Toby's weren't either, saving all that rigmarole I described above. Mine were stuck solid, probably due to being wet for a while.

I took a quick look at Toby's machine and it's in way better condition than mine was when I got it. Mine looked as if it had been a beach tractor : ) Completely rusted up and darn near every single nut and bolt fought me, but I won because I have a gas axe : )

Depends on your definition of easy : ) You don't need to fully rebuild it, but to take up the play, at a minimum you need to pull off the right side final and remove a shim. The reason I say right side is because that's the side that the bevel gear is on so it's that side that takes all the load. You can remove the rear cover which is only six bolts and check the float. In theory you would remove both finals but I'd wager it's only the right side that needs adjusting.
So split the track, drain the final oil, remove the clutch hub (need a 20t ram for that), and remove a shim or two from behind the bearing cover until the float is eliminated. All of this is easy if it all comes apart easily, like mine would now that it's been fully apart. Unfortunately Cat didn't have the approach of easy maintainability with these machines. For example, they could have designed those bearing covers to be adjustable rings like on a differential that were accessible in a way not requiring final removal. For that reason, I pulled my tractor completely apart because I really didn't want to dive into it multiple times (aside from my pony pinion that I've been into four times now in bids to make it perfect.....)
Risk level is unestimable because we don't know how much float your bevel gear shaft has, but if you remove the rear cover, you can measure the float with a dial gauge and pry bar. That should take you all of about ten minutes to check. Total swag on my part but if your float was say 005, then I'd say just monitor it manually if you don't want to fix it. If your float was 020, I think I'd want to fix it because although you have to do about as much disassembly to adjust the float as you would to replace a broken bevel gear, if you also have to replace a broken pinion, then you have to disassemble the transmission. Not a big deal but still one more thing you'd have to deal with. One thing that would concern me is how much more stress and wear rate increase would be applied to the pinion bearing. If you have an older D2 with the plain pinion ball bearings, then those are not very good at handling the thrust, so much so that Cat came out with a field replacement for older tractors that replace those ball bearings with tapered roller bearings. I'd love to get a hold of a pair of those field replacements for my tractors simply for piece of mind.