I fully appriciate your frustration Krynkle, I thought it was just me that couldn't see how this was a replacemennt service for "YouSend". Then again I can't say I'm surprised as since the release of Adobe CC last year things seem to have gone downhill fast at Adobe and I'm seriously starting to question advocating Adobe and its services to customers or colleagues.
It all started out so well with the launch of Adobe CS6 back in June 2012, then came the so called upgrade to CC with native 64Bit in particular InDesign which one might have thought would have ushered in a bright future and meant you'd be even more efficient. However quite the reverse, InDesign 64Bit is problematic to say the least, it's type handling is dire, its slower than the 32Bit version by a large factor. Not really what you would have expected from the prememinent company Adobe is held to be.
New features are fine, we all want them. But fixing the shortcomings in the Creative Cloud should at the very least be the main focus if it is to remain the publishing service of choice. I hope that Adobe find it in themselves to reflect on the roll out of CC and make strides in ensuring we don't suffer such and poorly managed roll out for the future.
Good luck and I hope they fix "Send" to be evrything "YouSend" was only better - not worse.
I also share similar frustrations with Send. I have to wonder about what it the heck Adobe is doing.
Send has all sorts of irrelevant junk attached to it but seems to have problems with the fundamentals -- like sending files, lists of emails etc. Cute, unhelpful error messages are maddening. I have had repeated problems sending large files ~ 100 MB or so zipped. I had to zip the files because Send assumed the binary files were some file type that they were not and so changed 'em grrrr!!!
Send repeatedly fails to send the files whereas the old standby Sendnow works just fine. Returning to your workstation after a couple of hours and seeing a message informing you that the files you thought were being sent while your were gone had failed and telling you "try again" is TOO MUCH. Why should I "try" again when it is Send that is the problem. What year is this where I need to "try" to get a computer to do things.
Over a couple of years of use I have NEVER had such a problem with Sendnow. So the Adobe suggestion that if you have more than 50 file you should just zip 'em is baloney because what you will find is that zip files will often fail.
I have other things to do and really don't want to take the time to evaluate other platforms but it appears that Adobe really isn't serious about this type of service and thus I guess I will have to do it.