Hi Carrie, I moved your question into the Jive Support space because I think you'll get a more timely answer here. I think that option 2 you list above is probably the easier option because in option 1 you'd have to ensure that the person is a member of the community and has access to the private group. Now, let's see what our support people have to say...
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Thanks for raising this question for sharing content with external users. If the user is already registered as an external user (in some versions of Jive, this is known as an external contributor), then this user will only have access to externally accessible private or secret social groups. Content residing in other places (e.g. open social group, space, etc.) will not be accessible to this user.
If you choose to share a document with this user or an email address (someone who isn't registered), this should generate an email with a PDF version of the same document.
I hope this helps. Feel free to test this out and let me know if you had any other questions on this.