The first idea that came to me, is to add a technical field on account (flag, default = false). Extend your CSV with the new flag, set for all = true Update accounts Extract contacts with condition where Account.MyFlag__c = true update contacts Delete flag (since not more useful)


When you upload Files there is "PathOnClient" field I think, you specify it and DataLoader will use it as a location for a file. You upload those files as ContentVersion and then to link them with the account you separately upload ContentDocumentLink records. Keep in mind that you can upload ~100k Files a day P.S. after you upload files result "success" ...

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