Jim,
I am so sorry - I missed your response on this. I know it's been six months, but the problem reared it's head again.
If I understand correctly, you are saying that the combination of NAT port forwarding and 1:1 NAT to my virtual IP's assigned to the CIDR block "could" be causing the issue when you say this "… if something happened to the port forward then it may misbehave.".
It's a weird too as often getting the remote user to clear their browser cache causes the problem to go away - but other times it takes a day.
We had been using NAT port forwarding in conjunction with 1:1 NAT to try and conserve our static IP's - but it sounds like it might be safer to just do the 1:1 NAT and not port forwards.
Is there any way to further pin this down? I have correlated Chrome browser network requests, with pfSense firewall logs and the request logs on the two web servers involved. I can pretty clearly see where the first six requests from the browser are all to the IP address of the first web server, but pfSense shows the sixth request gets NATed to a different server - but of course no rationale for why it did that.
UPDATE: Yes we are also using aliases a good bit. What type of issues might that cause?
Thank you again - Richard