Outbound SSL question

Potentially not the outbound connection. The remote site is after all receiving a port 443 request from your server through your local F5 (and firewall), correct? So if the F5 is in front, you should be able to observe this traffic leave its external interface and whatever response arrive back on that interface. A good guess that you'll probably see the response here, but that you might not have your VIP configured to pass this traffic.