Best way to send lots of email

[J. Landman Gay]

I told a friend I would try to help him set up a little database that 
sends email to a list of opt-in customers. To begin with there will only 
be a few names, but he is hoping that business will grow and there will 
be a few thousand eventually. I thought I'd just set up a simple stack 
that uses the excellent libSMTP to send the emails.

To protect each customer's privacy, we'd prefer that emails are sent out 
individually, or else in some way that doesn't display the other email 
addresses. That means we can't use CC lists. We could use BCC instead 
but then the recipient's name wouldn't be in the "To" field and some 
spam filters might block it.

If we send each email individually it could conceivably take a long time 
when the list gets larger, and spewing a lot of email at once could 
trigger an ISP's spammer alert. Does anyone know how many emails it 
takes before you look like a spammer?

What's the best way to handle a private mailing like this?

-- 
Jacqueline Landman Gay         |     jacque at hyperactivesw.com
HyperActive Software           |     http://www.hyperactivesw.com