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If you do decide to go with an email delivery service, here are some things to look for. Pricing, for example. You can either pay by the month, or you can pay by email sent. If you send infrequently, paying by the email sent might be more cost effective. Another question to ask: Do they fire customers for spamming activity? For example, one of my customers uses MailChimp and when they have too many unsubscribes every year or so, MailChimp sends an email to my client alerting them that they have too many unsubscribes for their email newsletters compared to other clients of MailChimp.
Another question to ask: Do they have at least one staff person who actively works with spam blacklists and whitelists? Equally important, can you talk to that person? Do you like their reporting tools? Do you like working with their application, and who are their customers? You might even ask for references if that's important to you.
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