At the main office I have configured the asterisk servers IP address as the DMZ host in the linksys firewall. (so absolutely no traffic gets
blocked).
— Whoa, what a security risk. You only want the SIP port open going in and out. Does your firewall have Nat on it? Check the logs to see what is happening to the requests.
At the remote office I have configured the IP address of the SIP phone as the DMZ host for the same reason.
— Does this firewall have NAT on it. Are you able to view the logs to see if the requests are getting through it. Check your firewall logs to see what is happening to the queries.
— Since it is a remote office you might check on getting an old pc to act as an asterisk server so you can setup IAX between the two.
If you get it let me know how. I have been struggling with the exact same issue. SIP just does not like NAT. NAT on both ends is even worse but apparently it can be made to work without DMZ anywhere. There are all sorts of suggestions all over the place and I have probably tried every single variation of them.