I'm not too sure about the multiple restarts, but if any of the BB's had a different version of google maps on them prior to you trying to push it out wirelessly, it will remove the old version, but not install the new one and it will just sit there at install required.
If you manually install the same version that you have on the server, it will report "updated"
My opionion is that the wireless app push doesn't work. There are too many flaws and exceptions. It is designed to be used on new devices and not ever be modified.