Hello Jordan,
Welcome to Microsoft Community and appreciate your time taken for sharing detailed information. I understand that Sorting Emails in Sent Folder. I could share with you some of my thoughts on this issue.
You could click By To in the last column of the drop-down options to see if there is View Settings.

And then choose Sorting items by... You could select by recipient name. Or click Group by...then select recipient name.

After clicking By To there are several options for you to choose, I don't see an option with an email address, which is where it falls short. If in the above way, your outlook still does not display the view settings, could you take a screenshot of the image after you clicked By To and show it to us so that we could better understand your problem?
Feel free to post back if you need any further assistance.
Best Regard,
Kevin | Microsoft Community Support Specialist
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