When I try to update a workflow that is bound to a content type, I get an error "There is already a workflow association with this name".
Since it is an update, this should work. I got the code here:
http://msdn.microsoft.com/en-us/library/microsoft.sharepoint.spcontenttype.workflowassociations.aspx
if (myContentType.WorkflowAssociations.GetAssociationByName(workflowAssociation.Name, web.Locale) == null)
{
myContentType.WorkflowAssociations.Add(workflowAssociation);
}
else
{
myContentType.WorkflowAssociations.Update(workflowAssociation); //this always gives an error
}