The problem with the lightest is probably that its got a pink undertone (especially if they're marketing it to the irish redhead type). I have similar issues as my coloring is very pale/light but has yellow underneath it - is charitably 'olive' I suppose. Make-up counter ppl tend to look at me and attempt to give me medium-darker shades and then express surprise as we work up to the lightest-that-isn't-pink.

Very difficult to find shades - I thought Shiseido was one of the best, partly b/c it is an Asian product so prepped for light-but-not-pink skin.