This is a fairly common use case that we get requests for: the need to update your email list without losing sent history, custom variables, etc. Well we listened, and implemented a simple sync tool for email lists (will be available in a few days).
Now when you upload a CSV file into an existing list (using the Data Sync tool) two things will happen:
1) If the email address is new, a new entry is appended to the list.
2) If an email address already exists, all the custom variables will be updated with the entry.

Vivek Bhaskaran
Viraj Patil
Scott Zaleski
Aditya Bhat
Kevin Battey
Sanket Shekdar
Rob Hoehn

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