I am running a Debian VM (Ubuntu or some other OS should be just as effective) with Dropbox installed with storage mounted via NFS. New files show up as quickly as expected. New data that I copy in within the VM is synced quickly as well. New data copied outside the VM, in FreeNAS space, does show up in the VM if I look for it, but it's not detected as new by Dropbox. So I wrote a script that looks for new data and touches it to update the access time. This is enough to notify Dropbox about the new data and it syncs. I run that script via the VM cron every five minutes.
I can post the script later today, but it basically looks for files that are new than a sentinel file that is outside the Dropbox folder. For any that are found it touches the containing folder with a time that is equal to the modification time of that containing folder. It then updates the sentinel as well.
The effect of this is that the modification time remains unchanged, but the access time changes. That's enough to notify Dropbox.