Hi SPF,
Heres my setup.
External DNS via DynDNS (static DNS, not DHCP).
Internal DNS via BIND server.
External DNS resolves mail.foo.com to WAN IP.
Internal DNS resolves mail.foo.com to LAN IP (non routable addy).
I use 1 cert on my Zimbra server from GoDaddy.
The cert is keyed to hostname, not IP addy so as long as both WAN and LAN clients hit
https://mail.foo.com, you are fine.
I'm pretty sure all certs are this way (keyed to host name) and not keyed to IP.