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How do you manage/translate the "This field is required" message and other validation error messages?
That's the ValidationMessage property of the field in the descriptor.
How do you handle the translation of drop downs, checkboxes (multi-selects)?
Similarly, those will be in the PicklistValues property.
Related to question 2, is it possible for us to translate the stored values or is this method just for front end translations?
You can translate just the value or the label, too. All up to you.