You can just tell him the amount or actually he should know it from his own records.  He doesn't need to get or enter the actual 1099Misc.  He just reports his total income on his schedule C.

Encrypting the email sounds like a good approach.

After much googling, I found IRS publication 1179.

Section 4.6 addresses the electronic delivery of 1099 (and other) statements.  Section 4.6.2 says that the recipient must consent to receiving electronic delivery, and must do so electronically to show that they can access the statement in the electronic format. 

It seems like most people who choose to issue 1099s electronically do it by posting the statement(s) on a secure server.  The recipient logs in and provides proof of identity in order to receive the document.  Nothing says it can't be done by secured email, but I supposed the request then would have to come by email, and there would have to be some way to be sure the email address belonged to the intended recipient.

If you mail the 1099-MISC using the US Post Office, it is considered delivered by you when you drop it in the mail - yes, even if the recipient doesn't receive it. That's the special status of USPS.

If you go the electronic route, then you have to prove (if it becomes necessary) that the recipient actually received the email or electronic delivery. 

For systems that host the completed forms online, you can do that if you have a login process that records access to the actual form - any commercial system should do this. But if you post it on a website and tell them where it is, you don't have any proof of delivery.

Ditto with email - you have no proof of delivery unless you ask for a positive confirmation from the recipient that he/she got the 1099-MISC - yet more emails.

but how can you prove that you actually mail it if you are using a regular envelope and stamp?

A certificate of mailing is a receipt that documents the date a mail piece was received by the postal service for mailing. You can purchase a certificate of mailing at the post office when you send out a package or letter.