I'm not sure you can say that. The winter ratings are only for the specific temperature where they are tested. So for example unless you're cranking at -22F or lower, then you can't really make a statement about which is thicker or thinner. I think you're getting lost in the weeds. You can look at KV100 which will tell you the viscosity at 100C. Sometimes they list KV40 which will be viscosity at 40C.
I think your #2 is accurate. I would not worry about it. For choosing an oil, you just need to look at your cranking temp. If you're cranking below -22F then you need a 0W-xx. Next, pick your grade. 30 or 40. Then put them together, and that's what you should shop for.
The question of oil quality is separate from winter ratings discussion above:
This holds true still.
Now, the exception is if you're buying AMSOIL or HPL. They DO NOT cheap out on base oils even with 10W and 15w oils (and straight SAE grade oils for HPL), so there's something arguably to be gained by using the highest winter rating you can. So for example for me, I would try to get by with a 10W-30 oil because I can squeak by in the winter even though I live where it gets cold, because it will have significantly lower VIIs, lower Noack, and theoretically lower deposits.
Hope this helps.