If bulk selecting, you should always see some sort of confirm dialog. On single orders you may not (depending on your email/config settings).
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If shop config set to 'confirm before sending', confirm the change in a dialog with a 'send email' checkbox and email text box for editing the email content
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If changing an individual order status and config set to 'send automatically' or 'never send emails', don't show confirm dialog.
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If bulk selection and 'send automatically', show confirm dialog with 'send email' checkbox automatically checked
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If bulk selection and 'never send', show confirmation but don't ask about emails
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If you have selected orders that are already the status that you're changing to, output a message and checkbox saying "X of these orders are already set to they may have already received these emails. Do you still want to send emails to these customers?"
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The email content in text editor is processed with order data if individual order (displayed with real order info). If bulk orders selected, it will display the email with the placeholders.