Surely, I pretty much use an 11/16" bit as far as I can go, then switch to a smaller 5/16 inch bit and extension(s) to drill a pilot hole out the other side of the stem. This bit fits the drill bit extension(s) end with the retaining screw (and sometimes a couple Hail Mary rounds of electrical tape) and lets me get thru the biggest stem diameters I've had these parts and out the other side. Then I go thru the other way with the bigger bit to finish the hole for the EHS cable. It's just a matter of monkeying around with bit sizes that'll fit the extensions and the diam of cable you're using a la ANSI - they give you a 1/16" tolerance I think it is. You're right, trick is getting the larger diameter hole thru far enough you don't bottom out the extension. There are some
really long auger bits too if you hunt around for em.
Log home builders use all sorts. Just gotta hunt around a bit (sorry)!
Had some EHS cable feed nightmares in trees like spruces which have flooded the hole I just drilled with sap/ pitch/ goo. I found that Olive Oil on the cable helped in these cases feeding the cable, but it still was a pitch fest. Wouldn't use motor oil or anything like that though.