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Number-cruncher: obsessive, quintessentially - retypes second time (8)

Ross

I believe the answer is:

annalist

I'm a little stuck... Click here to teach me more about this clue!

'second time' is the definition.
The answer and definition can be both people as well as being singular nouns.
Perhaps there's a link between them I don't understand?

'number-cruncher obsessive quintessentially retypes' is the wordplay.
I cannot really see how this works, but
'number' could be 'list' (synonyms) and 'list' is found in the answer.
The remaining letters 'anna' is a valid word which might be clued in a way I don't see.
This may be the basis of the clue (or it may be nonsense).

Can you help me to learn more?

(Other definitions for annalist that I've seen before include "Chronicler" , "recorder" , "one for keeping records" , "Historian" , "Narrator" .)

I've seen this clue in The Guardian.
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