We have discussed this in private before, but thought it'd be prudent to create an issue ticket for tracking.
AFAIR, Walk With Me expects there to always be some level of data available in the database before it's able to start uploading data. As we do not have any data, it fails, never uploading its data. I have a PAL copy and can probably setup a WEP AP with some pain if necessary, but @sepalani also has a PAL copy.