Hi Casey,
I don't believe Bruce has managed to get Subject Alternative Name (SAN) checking into NetTalk, yet. I suspect what you were running into is one of the servers that Twilio uses to receive requests could potentially have a certificate where the Fully Qualified Domain Name (FQDN) used to reach Twilio is listed as a SAN of a larger certificate, rather than the Common Name (CN), or primary FQDN, on the certificate. Most browsers won't complain all that much as long as the FQDN it's reaching out to is listed either as the CN, or a SAN, because they have that checking built in.
We'll get there, someday. Until then, your workaround is the solution. I prefer to make this toggle an option for the user, so they can decide if they want to accept the implied risk of not checking the CN; but I hate encouraging less secure habits like that.
As for billing for SMS ... FWIW, my personal suggestion would be to simply offer your customers the ability to supply their own access token to the Twilio service, and they buy the service directly from Twilio if they want to use it. That may not work with your application model, I don't know. For our SaaS offering, we will provide a "default" configuration that can be overridden by our customers if they don't want to use our supplied configurations, but we pay for the "default" services directly and consider it a cost of doing business.
Regards,
Flint