A couple of things came to mind when I started reading this thread, both quotations in an essay by H. P. Lovecraft. The first is a position of Lovecraft's own, the second a statement by a former president of Brown University:
1.) "The literary genius of Greece and Rome, developed under peculiarly favourable circumstances, may fairly be said to have completed the art and science of expression. Unhurried and profound, the classical author achieved a standard of simplicity, moderation, and elegance of taste, which all succeeding time has been powerless to excel or even to equal."
2.) "He [Lovecraft's opponent in the debate] seems to typify the spirit recently referred to by President Faunce of Brown University, who declared that most of us are 'too desperately contemporary'."
Now, this isn't really quite fair to Ian, though I think there is a certain relevance to his position in each. The first, because much of what I see coming from you, Ian, is almost an inversion of that; the second, because I also see a fair degree of too much focus on precisely that quality (or fault, as the case may be).
However: having read both the post linked in the opening post and the ones you brought in, I must say there is a fair amount of truth to what you are saying. Certainly "Doc" Smith's Lensman has all the faults mentioned -- even Heinlein noted that aspect presenting Kinnison as essentially cardboard in The Number of the Beast. Though having a fair degree of affection for the series, as for many other things from the field dating from the period it began (it continued for many years afterward), I would certainly not suggest it as an opening to a reader new to the field, unless I knew from experience that it was the sort of story/writing they would enjoy. And for someone with a low opinion of sf as literature -- um, no.
(I'd have to say the same about Ringworld, frankly. There are some good things in the "Known Space" series, but literarily, Ringworld is not one of them.)
On the other hand, I find it interesting that Ian doesn't even bring in the point about "Nightfall" being heavily metaphorical and addressing various of Asimov's concerns about society and religion/mysticism, etc. (the benighted theme, as it were); a theme common to a fair amount of his work. To be honest, even then, the story is too heavy-handed, and the writing is certainly far from Asimov's best, nor would I consider the story itself as among the man's best work. Nonetheless, I think it deserves a wee bit more credit than Ian gives it here. Not a huge amount, but a bit.
However, I do think there are a number of sf "classics" which would be perfectly fine to give to new readers: Flowers for Algernon comes to mind, as does A Mirror for Observers; Earth Abides is a good possibility, at least to anyone who has read any older literature outside of sf as well. A Canticle for Leibowitz; quite a bit of Fritz Leiber; I've run into far too many people turned onto sf by Heinlein to dismiss him as worth a try (though again, one should adapt the suggestions to the individual); Stand on Zanzibar, for those who don't mind a little experimental writing (ditto for Dhalgren and The Cornelius Quartet). Quite a bit of Clarke still remains popular and a good entry to sf for newbies, as well. Ellison, though less known now than some years ago, when introduced to people, often catches their imagination and not infrequently moves them quite deeply. Several of Asimov's stories also have their charms for new readers, and at his best his prose is not only serviceable, but at times quite good -- more subtle than he is often given credit for, and people tend to forget how often (given the "hard" sf aspect) he wrote allegorical tales, for the matter of that.... And then, of course, there are PKD, J. G. Ballard, a number of things by Aldiss, The Chrysalids (which would seem, in many ways, to be extremely relevant to our time... as it has been in the past), and so on, and so on....
Even some of the minor lights have their moments. Raymond Z. Gallun, though no master of prose, could both tell a good tale and be quite moving at times; C. M. Kornbluth remains as powerfully astringent as ever; Kuttner and Moore still maintain a high degree of literacy and verbal (as well as emotional) magic at their best; the same can be said for much of Sturgeon; Leigh Brackett wrote some wonderful sf adventure tales which hold up quite well.... Heck, even John Campbell (not my favorite writer by any means) produced some very powerful shorter tales: "Twilight" deserves its reputation as an intense mood piece, and shows a poetic imagination to that man one would seldom suspect.
And the list goes on. All of these, of course, have their faults. All have their virtues. With some, the prose is quite flawed; with others, it is evident that they were influenced by literary classics in their formation, for they use the language quite well and have a mellifluous and memorable style. (Bradbury often falls into this class and, while I do not feel Fahrenheit 451 represents him at his stylistic best, I agree with Dave as far as his ability to have a finger on the pulse of society, and see where we were heading.)
I think you have some very good points, Ian, and I agree with much of what you say; but I think you overstate the case a fair amount, as well. But, as I noted above, I think it is always best to adapt one's suggestions to the recipient, rather than merely throw out one's own favorites....
Oh, and I don't know as I'd suggest any particular novel; my suggestion is to try two or three different types of anthologies; that way they get a taste of a variety of writers and their approaches, as well as different eras, so they can better judge what aspect(s) of sf are more to their taste....