Maya, I'll take a crack at explaining what you're coming across. The only real way to know what category someone falls within is to actually see how their skin/eyes/face "reacts" to certain colors. There are actually professionals who do this by putting different colored drapes on a person, to see which colors brighten that person's look. Based on that, they determine what category they fall into.
So I think that part of the issue with seeing celebrities who don't seem to fall within the category someone gave them is that the "expert" who did so really has no idea how that person would look if draped in different colors, and is therefore just taking her best guess on what category that celebrity falls within. There is a similar problem when we try to categorize ourselves. All of these charts point to hair, skin and eye color, but at the end of the day, those are just rules of thumb, and the only real way to know what category you are is to test out the colors and see which work best.
This is why I think a lot of us feel we don't need color typing: we naturally choose the colors that brighten us up and look best on us. So maybe for someone like you, it makes better sense to look at what colors you feel are your best, and work backward from there. I see that you did that, and found that you hit three different categories. That also makes sense, because a lot of these categories are hybrids and kind of "flow" between each other, so someone who is a deep winter, for example, should be able to wear some colors that are good for deep autumn.
I think that another issue is the whole warm/cool thing. Some categories actually aren't really "warm" or "cool" at all, but are actually more neutral. I know that the soft categories are like this, and I believe that the deep ones are as well. So that could explain why people who appear to be warm are falling into the cool categories. I have also read several places that say that olive-toned skin is neither warm nor cool, making it more difficult to categorize. I do agree that these categories are far more difficult to apply to people who aren't Caucasian. It often seems like people of color are just an afterthought. I'm actually having a lot of the same problems categorizing myself that you are. I'm okay with it because I feel pretty confident in the clothing colors I wear, but I would really love to have more direction with makeup, so I continue to play with it.