Is it possible to set Outlook 2013 to do an automatic read receipt request for one particular user I send to on a regular basis?  I don't want read receipts requested for everybody I e-mail - just this particular one.

Thank you!

Use Rules.  Apply on messages I send > to people or group > notify when read.

It's always the easiest answer that is the best!  Thank you.  I didn't think of the rules.  I usually use rules for received e-mail instead of e-mail that I send.........

You're great! That helped me, too.

Can you answer specifically for one sender as well? For example I want to always send a read receipt to this sender but want the ability to choose for all other senders.

For returning receipts? AFAIK, no, not automatically using rules.