Nice pics, Bill.  You asked for ideas.

About the insulated tube under the waterer, in IL  I would use one insulated piece but only for the top 4 ft section. use regular plastic culvert for the lower 4 ft section where you want the ground heat. Run the insulated culvert up to the top of a concrete pad which is a foot larger than the waterer all around and 4" higher than the rest of the pad. This is to keep the cattle from backing up to the waterer and taking a dump in it.

Don't forget to drive an 8ft ground rod just outside the culvert before pouring the pad. Leave the ground rod sticking up a couple inches above the culvert and pad but inside your waterer base. To ground your waterer heater electrics and avoid stray voltage in the waterer. Driving one inside the culvert doesn't help much since that should be air down to near your pipe level.

As for the pump I would use a big Gould std pump with a BIG integral concentric pressure tank buried at the top of your casing and backfilled with sand. I forget what this type tank system is called but they are about bullet proof.  More difficult to install than the smaller tank your well guy wants to put in but worth it. jmho.  Good luck.  Jim at Dawn