I disagree with the "Dropbox, iCloud, Google drive" thing. Nobody is using them as a platform to work their files on, but more as a quick way of sharing files. not reliable to store or else.
Definitely not "nobody". I've had several clients where the dropbox folder was where work got done. For all of my non-git and non-movie projects, dropbox is where the files live and are worked on.
When a friend had his laptop stolen he said that it wasn't a big deal other than the money lost, as 90% of his files were in dropbox or Google drive.
In my world at least, this is the way the wind is blowing.
What about sharing - heavy - files with coworkers not using this app? What about uploading files? It feels to me like working in a bubble... but maybe I'm wrong.
How about some sort of dropbox like syncing? Put your files in a shared dropbox folder, sync dropbox folder on remote VM, save your work on remote VM when done, changes get synced back to shared dropbox folder.
Obviously not perfect and obviously problematic if lots of people try working on the same file at the same time, but should solve at least some of the problems.