Before a reboot, my Dropbox is fully synced.
After I reboot, I get a message saying that Dropbox needs to set permissions on my Dropbox folder, and then it does a full resync check of my very large Dropbox folder, which can take hours or overnight on a slow connection.
The problem may be symlinks set by older apps (Dropbox does not support symlinks INSIDE the dropbox folder as of 2019).
find ~/Dropbox -type l -exec ls -lah {} \;
And then unlink
them.
However, in my case it wasn't this, it was that some files were set with an unusual flag "immutable".
To fix: shutdown Dropbox app and app menu.
sudo chflags -R nouchg ~/Dropbox
sudo chmod -R u+rw ~/Dropbox
sudo chown -R christophera ~/Dropbox
sudo mv ~/.dropbox ~/.Trash/dropbox.old
sudo mv /Library/DropboxHelperTools ~/DropboxHelperTools.old
You also may want to consider deleting the old app and reinstalling Dropbox after these shell commands.