I sent 69 files with Send Now and was successful. Tried the same with Send but was limited to 50 files.
The upload progress bar in Send Now is useful as it shows the progress of each file. The one in Send dims the window and shows only the overall progress — less is not more.
Clicking on Send Now's link can download all the file at once which is the only option. Clicking on Send's link shows thumbnails which is better as one can see the images and be selective about which files to download. Send creates its own order for displaying thumbnails, not by file name, not by date and time, and not by file size — not helpful.
Send is not ready for prime time.
I agree, the 50 limit is rubbish, and it says now we need to upgrade to have more than 50... Less is (costing) more, it seems. Come on Adobe, answer the question!
I apologize for the confusion on that message. Upgrading will NOT permit you to send more then 50 files in a single transaction. (There's an engineering request in to fix that dialog.)
If you want to send more than 50 files, you can zip them up into a single file and send them that way. (Note that zip files aren't previewable by the recipient. They need to be downloaded.)