To check for coolant in the oil, let the tractor sit overnight, then carefully loosen the oil drain plug over a container. Back out the drain plug until it is nearly out, then carefully remove it only slightly from the pan. You want to get a few drops, not dump the oil.
If there is coolant, it always comes out first, as it does not remain mixed with oil, it seperates if you let it sit. The coolant will be at the bottom, first to come out if there is any.
If there is, hopefully a head gasket will be the cure;however it could also be a cracked head or (yikes!) a cracked block.
Next let's say this check shows no coolant in oil, you can sometime smell the diesel fuel in oil if dilution is bad enough. The first item I would suspect would not be o-rings, but an injector nozzle that doesn't seat. The tractor may still sound ok and run fine, but a leaking injector nozzle will still allow enough fuel into the cylinder to show up in your tractor's oil.
The best way to know is to remove the injectors and take them to a diesl service center near you. They will know what to look for and have the right test equipment. This service is not a big expense (testing the injectors) and if a nozzle or three is worn/bad/leaking all that should be replaced is the nozzle, not the entire injector. Not sure on the Kubota/Cub price, but many nozzles are ~$80 per cylinder. That is the most cost effective fix; think of it as $$ spark plugs in an import car.
I'd call around for pricing to test the injectors, some places are much higher than one down the street so do some calling first. Some Cub Cadet dealers are now set up for this. Typically the Kubota shops are more $$ I just don't believe you have an o-ring failure based upon your description. And remember, if it is an injector diluting that oil, it is also washing oil off the cylinder walls, so don't delay in repairs.