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Asterisk was setup with local, 4 digit extensions. My DIDs from the trunk provider came into the SIP registration endpoint, and the admin panel with the provider allowed setting up virtual numbers. Each DID was mapped to a virtual extension with the provider which was then used in the Asterisk dial plan so two devices could have different DIDs and default outbound numbers (e.g. simulating two completely different lines).
I had Asterisk's TLS and RTP ports exposed to the world so I didn't need VPN on the client devices (non-TLS SIP port wasn't exposed). Client softphones were configured to use SRTP for media security. The exposed SIP port necessitated setting up/tuning Fail2Ban to keep spam / brute force attempts at bay.
I did get text messaging to work within Asterisk (SIP client to SIP client), but not through the VoIP trunk. The SMS/MMS endpoint from the trunk was a REST API that I could not get integrated into Asterisk. I had some minor luck getting the SMS REST API bridged into XMPP, but I couldn't get XMPP to bridge to Asterisk in a way that worked with the SIP messaging.
I just gave up on that due to lack of time.
Wow thank you for such an informative response!