Success!
Ok. After starting completely from scratch with a freshly formatted card (with the SkyViewUS folder), and a fresh install of datamanager I'm up and running.
After completely removing the datamanager code and ALL of its data (you have to search for it, the uninstall process doesn't remove it), I reinstalled it.
I then selected all the states and did a download. NOTE: I did NOT have a usb stick in the computer yet.
After the download completed I inserted the stick and let the datamanager ask me to copy the data. Select yes and wait.
this worked. I'm betting the *.sqlite file is being mismanaged or the state corrupted once you start interacting/changing selections in the datamanager. Hopefully its a simple fix.
If you guys can convince SeattleAvionic to upgrade their software to something more modern (and hopefully that would run on Mac also) that would be great!
Good Luck.