My first suggestion, is to always BCC yourself on emails, so you know that it went out properly.
As far as suggestions for how long to wait, it depends on the urgency of the email.
If you send an email that is time sensitive and think that for some reason it didn't get delivered, you can immediately send another email, stating, "I apologize if you're receiving this twice. I received an email error and wanted to be sure my time sensitive email went through."
If the email is not time sensitive, you can follow up 3-7 days after by forwarding the original email and putting in your new message, "Following up, to be sure you received the email below."
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