You are 100% correct, the localized URIs do not have wild card certs *.pstn.umatilla.twilio.com thus failing the handshake. I used the Termination SIP URI and it worked like a charm!
I will have to work with twilio to create wild card certs for their *.pstn.umatilla.twilio.com
$ curl -vv https://techguysio.pstn.twilio.com:5061
* Trying 220.127.116.11:5061...
* TCP_NODELAY set
* Connected to techguysio.pstn.twilio.com (18.104.22.168) port 5061 (#0)
* ALPN, offering h2
* ALPN, offering http/1.1
* successfully set certificate verify