Actually I'm just a big security fanboy hehehe, it's the greatest hobby ever. Cryptography has got to be the coolest hobby ever.
Cryptography is never, and can never be a "hobby". If you think so, you have no understanding of the issues involved in security, and certainly should not even be thinking of running a service.
The setup is nice an everything but the vBulletin track record on security is not that great. Everything else is useless if some remote exploit can reveal the servers ip address.
How is that possible when used in conjunction with TOR?
because you have access to the computers network if you have compromised the application software/database, thereby being able to obtain the IP address - particularly useful if you have uPnP enabled, and other unicast/multicast protocols on the network (dhcp, bonjour/zeroconf etc.). VMs can be susceptible dependent on the virtualisation configuration. Does a chroot jail ring a bell?
Just to be clear, OpenBSD is not, and never will be the securest Operating System. Whilst it does a very good job of being secure, it has no independent formal verification.
Please look up the terms Common Criteria, NIST, NSA, EAL (particularly EAL4+ ALC.FLR.*) and
Most importantly you seem not to have read the mailing lists and website that tell you how to do exactly what you want to do without causing problems. (hint. it's a VM solution, with a firegap.)
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