Calibre doesn't talk with the reb1100 or the ebookwise.
I'd also enjoy it if it did as the ebookwise is my usual machine.
At least with the reb you can handle the conversion to rb. For the ebookwise the conversion to imp it's not implemented yet.
As for DRM, as far as I know you have to strip the DRM yourself because calibre will not do it for you.
Search around the forum and you'll find hints on how to do it. Most of the formats have been "circumvented"
.