Data should always be stored centrally, either in the cloud (e.g., Dropbox, MS 365, Egnyte) or on an on-premises server (e.g., Windows server, NAS).
If we’re transferring a user to a different computer, file transfer isn’t included because the user shouldn't be storing files on the computer. If file transfer is needed or requested, the tech should let the office admin know so she can advise the customer that there’s an extra cost for data transfer.
Once the file transfer cost has been approved by the customer, the technician may need to verify that the data is not stored centrally (as the user may not realize their files are syncing to a server or cloud site). Once this is confirmed, it’s often advisable to do an assessment of the amount of data so we can determine the best way to perform the transfer and advise on the amount of time it’ll take.
Technician should advise user that, in the future, all data should be stored in central storage to avoid risk of data loss.
If there is only a small amount of data (on the order of a few megabytes), such as browser bookmarks, then it's acceptable to do the transfer on the spot.