No - the campaign will consider the current value. Static list is just a holder of that list - the records keep on updating. (If I am understanding your question correctly)
No, the upload is a point-in-time change. The record on the list is really only using the Marketo ID to determine who to show. If the person's record updates, it'll update the field on your list (the members of the list are static, the data within your list is not).
If you're using smart list filters to define your list, and the point of reference data changes (using your example, you only want users named "Jim"), the contact would drop off the smart list once it updates to James, and the static lists that include the contact will now list the name as "James," despite the fact that your original upload changed it "Jim." It's basically using the most-recent data on his record, not the upload as the data source.
Hope that helps!