Sending Email Using Automator and Mail

Every year I shave my head for a charity called St. Baldrick's. I raise money and then send pictures to all the people who donate to me shaving my head. I was wondering if there was a way to send a group of people an email with attachments in automator. Not only this but something special. Many email programs will mark something as spam if it is send to more then four people at a time. I would like to have an action or something in automator so that I can specify who to send it to and then have them sent as individual messages. This can be a real pain even if I were to copy and paste stuff. Is there a way to make my life easier so this doesn't take up so much time?

I ran accross this randomly so sorry if this is irrelevent with timing. It seems however that Text Expander might be what you need. It is a mac program though, not ios.
http://www.smilesoftware.com/TextExpander/

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    Hi guys
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              if(smtpSocket != null && os != null && is != null) {
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    try {
    if(is != null) {
    is.close();
    is = null;
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    i have used an example on the web to help me do this, so it may look familiar!!
    It works fine when i run the program in debug mode but doesn't work when i run the jar file, i was wondering if anyone could help me understand why? or give me a clue as to where to look as i have had the strange realisation that i rarely compile my code up to be used by other people!!
    sad but true! Also apologies if i haven't posted adequate information, this is the first time i have posted on the forum asking for help!
    Anyway help would be most appreciated and thanks in advance

    Sorry, by debug mode i mean running it using netbeans 5.5 and clicking on the "run main project" icon.
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    Creo que resolvi el problema, temporalmente.
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    2) Vuelvela a crear
    3) Ve a Ajustes
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    Puerto del Servidor: 25
    Lo consegui de aqui: http://www.emailaddressmanager.com/tips/mail-settings.html
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    I think I solved the issue, temporarily at least
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    Please try this out!!!!!!!!!
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    Hi
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    Please try this out!!!!!!!!!
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    If Len(aFrom) > 0 Then .Recipients.Add(aFrom).Type = olOriginator
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    .Send
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