They are annoying but aren't anything that'll stop me from buying something RTW that fits. I wouldn't ever ask for them on something MTM or bespoke. I think for most people, it isn't something that bothers them.
But that actually does bring an interesting point for this thread: what about items which are internally incongruous. That tie is a good example. It's fabric is clearly S/S, but the colors are very F/W. Another example of this is this slubby wool tie from Henry Carter: .Also, Darkside, that tie makes a very good knot. I have the plum version as evidence [[SPOILER]]
I definitely wear shantung in the winter. Only convention makes it appear to be a S/S tie. And I've probably worn a wool tie with a linen-wool jacket. Don't know that I've ever worn one with a purely linen jacket though.
I don't have much of a preference. A bunch of my shirts shrank a bit...enough to hide the cuff when roboposed...and it turned out that I wasn't even bothered slightly. I do like cuff with suits though, for whatever reason.
Vox's neat looks like a madder, which I think is fine (I'm thinking your more run of the mill printed neats). And I am not saying it can't be done. I'm just saying that doing so will require either a lucky combination or a lot of thought for an outfit that just isn't going to look wonderful, even if it is passable.
I think Boyer's outfit would look poorer in real life.