You would have a table that is a record of these people, or contacts.
A layout would be based on this table
A script would loop over each record in the table, and scoop up each name as it loops, and with each scoop, an email would be sent.
Make the table, the layout, then try your best to script the script. Post the script here, and let someone have a go at correcting it.
Within the loop you will create, the Send Mail function will contain the field names for the To: email address, subject line, and body of the email in which you can insert fields to personalize the message.
You can add one attachment to the email, but if you want to enhance fonts, you need to use a plug in to accomplish that along with other html formatting.