Attachment issues in Mail and Outlook

We recently started to upgrade computers to Mountain Lion (10.8.2) and have discovered a frustrating issue. Sending attachments from the mail app (.jpgs, sending zipped files is not an option) to PC's running Outlook (all current versions I believe), the jpgs come through as embedded, not as attachments.
Although this would seem minor, there is no way to:
A. Grab multiple files and download them. It's "right click file 1", "right click file 2" etc. and then B. The files then lose their original names, rendering them useless for the back and forth editing we need to do.
I've tried changing from Rich Text to Plain Text, Send Windows friendly attachments On and Off, and every other work around offered here:
How can I prevent mail attachments embedding when sending mail
How can I prevent mail attachments embedding when sending mail short of purchasing the "Attachment Tamer" because, come on, Mail has always worked before, why do I need to buy an add-on to do my work now?
Any thoughts or ideas, would be much appreciated.
Thanks

Big subject, so I'll let Kurt explain it;
http://www.jklstudios.com/misc/osxfonts.html

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