@MindfulCoyote:
Not to be pithy, but I think a diagram would be a great place to start. It would add clarity to your description as well as invite commentary. Aside from the additional detail it gives us, just creating the diagram can solidify your own conceptualization. Doesn't have to be fancy, but it should include your major goals like the server "DMZ" and split routing with as much detail as you are interested in adding.
You could include this info in the diagram, but lacking the diagram, some questions that I have based on your description are:
I'm not entirely clear on the topology. Are you saying it's something like:
(LAN1 & LAN2) –> Switch(es) --> pfSense --> Cisco --> (ISP1 & ISP 2)
What is the bandwidth of the various links (internet & internal). (pfSense will become a chokepoint in your design, not sure if a Netgate 7541 is up to it? I think the Netgate 7541 includes one year of support... maybe that's a resource for you?)
What is the Cisco model number and why do you want to remove it? (Cisco's are generally fairly reliable and generally quite good at doing what they were designed to do.)
Your flow diagram is correct. One ISP is currently 50Mbps and the other is 30Mbps. I will draw out a clearer diagram as soon as I can. As far as the hardware goes I was led to believe that it is more than enough for our needs so I hope that this is true. I will check with my Netgate contract… I know there is support but hadn't considered that they may actually help with the firewall setup beyond the basics.