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Leaving the Id blank will create a new entry. Having the Id of an existing item will update that item. You cannot change the Id of an item from here. If you use an Id that doesn't exists, the save will be ignored.
To have multiple image based items in a record, seperate by a pipe (|). If I had a language field that used flags (called English.gif, French.gif, etc) I would put "English|French" (Without quotes)