gdaydigger - if ADE is already on your Mac and your Mac has been authorised in ADE, then the drm protected books should open in ADE.
When you say you moved the books to Calibre, do you mean you moved the actual epub files or just the acsm files? The acsm is the book file pre-authorising by ADE, once a book with drm has been authorised by ADE on your computer (done automatically within Sony Library in the current verion) an epub file is created.
Try finding an epub file on your Mac, go to Get Info and set it to open with Digital Editions and see if it will open. If not, then within Digital Editions authorise your computer and try again.
However, and it is a big however, even if you get the book to open on your Mac, it will not work on a Kindle. Your books will almost certainly be in the epub format, which the Kindle does not read. In order to read an epub on a Kindle you will need to strip the drm and then convert the book to the Mobi format (Calibre can do the second stage, but not the first part).
I hope some of this may help.