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Email Templates: Including Data From Related Custom Objects

I have created an email template that reads both standard and custom data from the Contact object; no problem there.

But I also have a custom Membership object that I need to grab an expiration date from. The Available Merge Fields in the content editors show the Membership object and the field I need, and I can copy and pasted it into the content perfectly.

I have two questions:

1) The expiration date is not being pulled into the field in the template when I send an email. The Contact does definitely have a Membership object associated with it, and it has an expiration date. Why might it not be apearing?

2) A Contact could have multiple Membership objects as s/he renews over time. I want the data pulled from the latest Membership object only, the one with the latest expiration date. I don't see any way to do that in the email template editor. How can I do that?