The auto-announcements will do that when the first person enters the server and the server has been running for a while. That's exactly what it's doing.. "catching up". You're seeing the announcements that would have displayed to players had there been any in the server.
The only way around this is to set the minimum players to 1. This has the server sitting in limbo until someone joins it. When someone joins, the server runs the first map in the rotation and starts the announcements.
Your remote manager problem could stem from a number of reasons. The BBO RM should be giving the person trying to connect an error message. What is it?
My first guess would be wrong port. When your friend tries to connect.. have him use the remote manager connecting through port 3558 instead of what you have the BBO server rcon port set for.
The right version of the remote manager has to be the same version as the server version you're running. If you're running 1.10 the remote manager also has to be 1.10. If you're running the 1.08 version.. the remote manager also has to be the 1.08 version.
Also... if your friend is on Vista.. he may have to run the program as administrator by right clicking on the start up icon for the BBO remote manager.