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

I believe the answer is:
annalist
'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" .)
