If you want to use Outlook without any external services, there is a freeSend Messages Personally tool available. By using this utility you can create HTML email, attach required file(s), add all required recipients to "To" field and then run this utility right from Outlook ribbon (on the message window). The utility will create an individual separate message for each of the recipients.
There is also a tutorial video available. This video shows the commercial version of the utility, but it almost the same with the exception of support for macros.
DISCLAIMER: I recommend this tool because I'm one of its developers, so feel free to ask any further questions.
There is also a tutorial video available. This video shows the commercial version of the utility, but it almost the same with the exception of support for macros.
DISCLAIMER: I recommend this tool because I'm one of its developers, so feel free to ask any further questions.