Why do you have your VM win2k box on the WAN side. The WAN side should only be dedicated to your cable modem or adls modem. All other systems should be on the LAN side.
Details
pfsense VM picks up appropriate information on WAN via DHCP, and webgui interface status window shows that it is getting a proper IP, within the right subnet, and the right gateway / dns IPs
The above sounds good. My pfsense does this as well.
another VM, running Windows 2000, is set to the same Default Bridged config as the pfsense WAN interface, and picks up the correct info across the board as well; further, it can browse the web just fine
Why do you have this on the WAN, the only thing on the WAN side should be pfsense especially if you're connecting a cable modem or dsl modem. Are you setting up some sort of DMZ area? Do you have another router infront of pfsense?
only difference in IP configuration between Win2K VM and pfsense VM is a different host IP from DHCP… they are getting all other settings from DHCP and they are identical on both (gw, dhcp, dns, etc)
setting pfsense's WAN interface to static IP in the appropriate range instead of DHCP, and manually entering appropriate IP info for gw and dns, does not resolve the issue
Win2K VM can ping the DHCP provider, and can ping the physical host box as well; as mentioned, it can browse the web fine
cannot ping the pfsense WAN IP from any machine on the subnet
pfsense cannot ping any other machine on the WAN's subnet whether by IP or by DNS name, nor can it ping the IP from which it says it is receiving its DHCP info(?!?)
issue does not lie with host machine IP stack or network config, and disabling all but for VMware Bridging protocol on the host machine's adapter does not resolve the issue
Host machine is Win XP Pro SP2, with all patches installed, and firewall has been enabled/disabled without changing anything whatsoever.
Here is my setup, kind of like yours but I don't use Win2k VM..
I have a Host Machine 2 NIC's
1 WAN ---> Cable Modem only
1 LAN ----> GigE Switch ----> Internal Network Client Machines
I have 2 VM's
1 VM pfsense, configured with 2 Virtual NIC's, that Map to Physical WAN, and Physical LAN.
1 VM Debian configured with 1 Virtual NIC Mapped to Physical LAN
I never use host-only or NAT (Ok I use NAT if im going to patch a new build.)
LAN is like vmnet2 which I point to my Physical Broadcomm GigE Nic in windows
WAN is bridged vmnet0 which points to my Physical Broadcomm Ethernet Nic in windows.
LAN 192.168.1.x
WAN is received from cable modem.
Now on my Windows HOST system, I statically IP my Ethernet NIC to 1.1.1.1 so it doesn't DHCP to the cable modem.
I IPed on my HOST on the GigE interface 192.168.1.10, and from there I can ping 192.168.1.1 my pfsense VM. Sweet.
My Debian box is mapped to the LAN interface which is the GigE NIC on the host system. I can ping 192.168.1.255 -b and I see everything, or nmap -n -T5 -sP 192.168.1.0/24.
I'm not sure if this helps but I hate seeing a message out there with no response, especially when I'm kind of doing the same thing I guess.