How to measure or assign hydrophobicity score values to individual amino acids of a PDB structure?
No, this doesn't makes sense (I think).

The hydrophobicity of an AA is the hydrophobicity of the AA, in whatever context, just like it's molecular weight. It's weight is it's weight, in a structure or in isolation.

I know this seems physically unrealistic, but so is an abstract measure of 'hydrophobicity', it's just the best we can do based on partition coefficients.