I'm a big fan of Frederique Constant watches for beginners:
Elegant, Breguet-inspired design, very affordable, and reasonably sized at 40mm.
Personally, no. But to be fair, I used to think the same about ties, and I've come around to the importance of high-quality silk and/or six-fold construction, as I've found that the best ties produce a better knot, knot more easily, and look substantially better. Will I have the same change of heart w/r/t socks? I think they are a less visual piece of the wardrobe, so I'm dubious, but never say never . . .
I'd go with Weymouth. The visual appeal of a wholecut is that the shoe is only made of one piece of leather, so it's as simple and minimalist as you can get. The Rosemoor strikes me as an odd compromise -- not a wholecut, yet will suffer from the shortcomings of one (e.g., more easily showing creases on the toe box).
Nice. I like the fit of their extra slims better than BB so am in the process of switching over to Tyrwhitt. I think the shirt quality is a notch below BB, but the fit is great, and picking up shirts for $50 a pop is pretty nice compared to BB's steadily rising prices (best sale you'll ever get now is like $60 a shirt).