Hi Rob,
Thanks for the explanation!
1. For ringing simultaneously, have you tried to set the call queue's call handing to "Simultaneous"? If not, try it and let me know. Unfortunately, this needs to be done via the service web dashboard only (not via API call) 
2. This is a bit tricky because by the system only lets you transfer unanswered calls from a call queue to a voicemail. I am thinking of a workaround solution (I have not tried this myself though) so you can try as follows:
- So e.g. you have 7 agents in a call queue. Make sure all of them should have the same call handling and forwarding rules by numbers of ringing.
- If you expect an incoming call to ring 5 times (25 secs) before you transfer the call to the level 2 group (if no one answers), then you can set the call handling for all 7 agents to ring for 6 times.
- Then you add an extra agent to the call queue and set the call handling for this extra agent to ring 5 times. And create a call forwarding rule to transfer the call to the level 2 group for this extra agent.
This way, the extra agent would acts as a call queue manager whose task is just to forward the call to the level 2 group.
If you have problem with trying this workaround solution, please let me know.
Hope this helps!
