Sorry David, I missed this one!
I think you are over complicating things by trying to view the half-whole (mode b) from the perspective of the whole-half (mode a). Forget the analysis of the whole-half (1,b3,b5,bb7) when doing this.
For example, if you have a Dbdim7 chord use C half-whole (mode b). This way you simply view the notes for what they are in relation to C which is now the root. So Db is now the b9, D# is the #9, E is the 3rd, F# is the #11, G is the 5th, A is the 13, and Bb is the b7. It’s basically a C7b9/#9/#11/13 chord! You can do this for any diminished chord. Because it is symmetrical in nature, any of the notes can be the root. You can therefore make the new root 1/2 step below any of them and apply the half-whole or mode b scale.
Let me know if this answers your question.