Network Infastructure

Second time writing this. Ok. Trying to get a good network infrastructure down here in time for next semester. Trying to make use of VLANs to simplify my life, get things segmented, make use of that Cisco 3550XL I bought ages ago. I am trying to integrate a management network into my infrastructure, move Proxmox over to its own subnet, segment PPTP users so nobody is poking around on my LAN, all that good stuff.

Unfortunately, I am having trouble with pfsense VLANs again. I followed the guides on the pf site and the directions in the definitive guide, yet I am not getting DHCP leases from any of the access ports I assigned to my VLANs on the switch. It is probably a firewall issue, or something in the switch I missed. I didn't sleep well last night so I am thinking about posting to reddit or something to get help with the issue since I really need to get this up and running and move on.

Anyway I made a small little visio this morning to illustrate my current config: