I'm application agnostic (lots of suites/apps out there), but my beef these days is with cloud and cloud security. Unfortunately this is a component that many companies seem to forget. They don't keep the stuff they need to keep secure secured. You want to keep it in the cloud for convenience, go ahead, but secure your stuff first people... I can't tell you how many times people send me documents which should not be stored unencrypted through an unencrypted transmission and then when I purposely extract/update/secure the document before returning it to them, they get all upset.

My preference is local, but backed up to an enterprise resource once encrypted. Seen too many breaches to not take the additional few minutes to protect the stuff. And if the customers complain, fully ready to give them the spiel and ask them if it's worth the breaches.

As to your last "question", I suspect it's not going to get any better. I still see people in large corporations guilty of lax password management (generally a file somewhere with 11-15 passwords that they cut and paste) for critical infrastructure... the larger tech corporations trying to make things more convenient for users (and not considering the consequences)... Cloud files are great for convenience, but once they've been copied and spied upon.... good luck.

Drives me nuts.