If you are going to use all Microsoft Products to create your DMZ, particularly ISA 2000 you need to keep one obscure thing in mind.
ISA 2000 does not support internal Domain Members in it's DMZ
INFO: ISA Server Does Not Support Domain Members In Perimeter Network...
Check out http://www.cacert.org as they are a non-profit Certificate Authority based in Austrailia and you can get SSL and email certificates for free by registering with them.
The use of multiple gateways can be configured to use Dead Gateway Detection, but the only way that it will check a gateway again that has been "declared" dead is if the gateway now in use also goes dead or the box is rebooted.
Multiple Default Gateways Can Cause Connectivity Problems - 159168...
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