Interesting post - I do colour analysis, but not with any seasonal system, but one that has 14 different colour directions (which can then be broken down again into 42 groups), based on Albert Munsell's colour theory and using the properties of chroma, saturation, intensity, tint, tone and shade.
What you see when the colours are flattering on your skin is that you look like you're illuminated from the inside. You will look younger, slimmer, taller, more vibrant.
Yes the seasons are outdated, but colour analysis done well is actually an invaluable tool. It also helps you create a wardrobe of mix and match outfits as you don't have orphans in your wardrobe based on colour.
The problem with the seasons is that they're too limiting - if you don't fit into one of their groups, it doesn't work, I've plenty of clients who have had a seasonal analysis some point in their life, and when we do it for them now, they are really pleased with the results as they like the colours and they can see how much better they look.
Also, your colouring changes your entire life, we don't usually have the same colour hair at 20 as we did at 4, and by 40 it is often different again, and by 60 again it has changed. Along with these changes, our eye colour changes as does our skin as we may lose some of the carotene and other pigments in our skin as we age. So the colours that suit us at 20 won't be the same as those that suit us at 45.