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For some reason @Rivendell_librarian's post keeps popping up again in my 'alert' though I've read it several times. It popped up today again. This seems to happen with other posts as well - I'm not sure why.
Since it did, I'll take opportunity to reply to Squint's here finally.
My dear Squint: It's most OK to be hesitant. And, it puts you in the vast majority of people. Generally, a comfortable place to be.
However, I'd be hesitant to assume Shippey's posture on the issue myself - for a number of reasons - stellar though he may be.
However, no remaining Ent is too big on 'seeking comfort.' (I know, because I'm the only one.) And we aren't quite as big on 'staying uninvolved in the affairs of the world' as we once used to be.
And, I'm hesitant just on my own accord, to agree with the good Shippey, mostly because I know better.
I of course confess - "That" is a very fine word, when used properly, and has a very fine and clear topic to which it refers. Though even properly used, it's still well overused. And often, even in its 'proper' use, it can leave a "multiple" of potential 'targets,' leaving the poor reader to try to sort out just which "that" is being referred to.
UNLESS of course, we're writing "that" in a setting where a person or people are speaking. There, it's best to show people as they generally really are - totally unaware of how to use "that" properly, plague that** "that" is. Otherwise our "people" don't come across as feeling genuine. We find ourselves thinking, "people just don't really seem to talk that** way." or "people just don't really seem to talk like that.**" And, we're absolutely right.
Tolkien's age was perhaps even less aware of the proper and improper uses of "that" than we are now. It is rampant among the writers of his age and earlier. Philology and Etymology were evolving and changing at an incredible pace - to a degree, being bypassed so quickly by time, we see many today consider them to be a nearly dead science. (Though they're not.)
And as Shippey spans his age and this one, and little to no improvement has been made in our use of the word, we should expect Tolkien to be lauded for his writing ability. The rest of Tolkien's writing was exceptional in many ways. Besides, Shippey referred to what Tolkien "knew,", not to what he actually employed, in the sense of certain particular words. His ability to construct his meaning through the building blocks called words was indeed pretty much unmatched. And it was in this sense he 'laboured over every word.'
So I will certainly not 'insist' on removal of "that" from conversation - verbal or written - though I only very intentionally make use of it myself.
But neither will I resist the urge to point out how much it is but a space filler in most cases, and though accurate, can still be misleading in others, and is most often overused to distraction.
Communication is, for me, an endeavor in precision. "That" is not a helper in the quest.
"That" is wasteful, and it is costly.
Tolkien could, in many places, have been clearer, and most likely reduced total production costs, had he attended to it properly. He certainly engaged no editors capable of helping him on the subject. (He had to battle with them over some much more basic things, I fear. I've not read him write anywhere of a need to engage them over the issue of "that.")
Thus stands the Perspective of the Ent. (Note - not an opinion. Fact based, and accurate. But we are also forgiving, especially with works containing 'redeeming qualities' even when saturated with the "that" disease.***)
**that - a properly used "that" in all 3 cases. The first two have as their target the precedent conversation about the way 'talking' was being done. Or even possibly just something like "I don't like the language he/she uses. People don't really talk..." &c. The third is a properly used "that", its target being the "that" immediately following it.
None of them are necessary, nor as precise as the communication could, and probably should, be. Though none of these would lead to any confusion, having only a singular possible target in view.
***disease - definition: "a disorder of structure or function in a human, animal, or plant, especially one that has a known cause and a distinctive group of symptoms, signs, or anatomical changes."
-- NOTE: In the case of "that" - the 'disease' works two ways.
-- Some find an absence of "that" a disease. Used so commonly, not to hear it sets up a void - an absence - a 'disease' for them.
-- Others find the presence of "that" a disease. Used so often, its waste and cost become the source of disease for them.
"That" is very much a double-edged sword.