@luckman212:
I can't be sure but from what you've described it sounds like your Charter modem is losing sync from time to time and reverting the DHCP that it's "passing through" to your pfSense router to a temporary subnet. This is a known behavior especially for cable modems and it can be very annoying.
It would be great it pfSense/FreeBSD handled this "bug" a little better but there is a possible workaround that you can try…
Try going into your WAN Interface settings and under "Reject Leases From" put 192.168.100.1
See if that makes any difference...
Thanks for this tip, I'll give it a shot. And also thanks for the references.
In my post, <wan ip="">refers to the dhcp IP assigned by Charter cable, not to 192.168.100.1. One of the references you linked mentioned accessing 192.168.100.1. I usually can ping that address when the WAN is 'offline', I guess that makes sense. Unfortunately, I have to access to the internals on that modem, all I can get at that address is signal levels.
For reference, my modem is a Cisco 3208 DOCSIS 3 with no wireless. I do not use a cable phone so it provides only internet to pfSense.</wan>