Thank you so much @stephenw10 . My boss insisted over and over and over again it was a PFSense issue, and while I was confident in the PFSense config, I, being the junior IT person I believed him. Your help got me the info I needed to convince him to look outside PFSense and wouldn't you know it, it was the windows Firewall that's his area that was the issue. The Windows firewall on the machines didn't allow ping responces outside their local subnet.
Thank you so much again @stephenw10 you rock!