Create personalized .pdf cover letters and attach each one to a corresponding E-Mail message in Outlook

This is a question that involves using Excel, Word & Outlook. Please direct me to the proper forum if necessary.

I want to send out personalized cover letters to each one of them via e-mail.

I have a cover letter word document containing merge fields linked to the Excel document.

I need to do the following:

- Merge the cover letter word document with the Excel spreadsheet to create 500 separate and personalized .pdf files of the cover letter, each with a filename derived from the name of the company (Ex: "Cover Letter - Toshiba"; "Cover Letter - Samsung")

- Attach each one of the personalized cover letter .pdf files to a corresponding e-mail message in Outlook

- The e-mail messages themselves must also be personalized using the same information from the Excel spreadsheet

As a result, each employer would receive an e-mail message similar to the following, with the "<< >>" indicating the personalized fields.

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To: <<*** Email address is removed for privacy ***>>

From: *** Email address is removed for privacy ***

Subject: Application for <<Sales Position>>

Dear <<Mr. Doe>>,

I would like to apply for the <<Sales Position>> at <<Toshiba>>. 

Attached please find my cover letter for your consideration.

Thanks,

Jane

Attachment: "Cover Letter - <<Toshiba>>"

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If what I have described is not possible using the methods I described, please advise as to what methods I could use that would not require me to do any sort of manual personalization (ex: attaching each document one at a time, naming each file, or having to merge several times). 

Streamlining this process seems like a completely reasonable thing to be able to do with Microsoft Office, I imagine many people do it now just by using brute force. I hope I won't need to do that.

Any help is appreciated!