So I was able to bring it down today. Upon the first reboot (VM running, just issued reboot command from root prompt) I was unable to ssh in and the web interface was not responding. I connected via the hyper-v console and was greeted by an "asterisk could not start" message. I was able to log in and run iptables --list which listed what looked like the default entries (local LAN ranges allowed through and ISP allowed through). So I issue the reboot command again and watch it as everything comes up. Looks like everything starts properly except I still cannot ssh or web in. I log in as root and issue the iptables --list command only to be greeted with the same iptables as before. So I run the add-ip command from /root/ and add another IP on my local subnet and magically a TON of entries show up when I run iptables --list now and everything works as expected.
This is not a huge issue except for the fact if something happens and the vm host reboots the guest and I am not where I can remote in and fix it. Any thoughts on this? I do have the "default" and after add-ip iptables I can send if needed.