It seems like the UserWise instance is not properly disposed when the editor stops playing the game, every second attempt to play the game there is a nullref happening and userwise can not be initialized.
Additionally, you have to manually unsubscribe to the EventHandlers like OnSessionInitalized, otherwise the subscribed events stack between sessions.
Every second session:
Event not getting disposed correctly and keeping subscribers between sessions:
It seems like the UserWise instance is not properly disposed when the editor stops playing the game, every second attempt to play the game there is a nullref happening and userwise can not be initialized.
Additionally, you have to manually unsubscribe to the EventHandlers like OnSessionInitalized, otherwise the subscribed events stack between sessions.
Every second session:
Event not getting disposed correctly and keeping subscribers between sessions: