Your sample file is obviously a sample file and probably doesn't correspond closely with a real life document. Do you want a solution that WILL work with a real life document or just this sample doc?

For instance, are there Questions that use manual numbering rather than automatic paragraph numbers? Are question 'blocks' always separated by empty paragraphs? Are there question blocks with no tools appended on the end?

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Andrew Lockton
Chrysalis Design, Melbourne Australia