What should I be diagnosing if I cannot use traceroute? Whatever
domain I try to check, it always times out. The box is behind a
hardware firewall. It also uses pf to some minor degree. However,

what do you mean "hardware firewall"?

pfctl -d does not allow me to traceroute either.

$ traceroute -v freebsd.org
traceroute to freebsd.org (69.147.83.40), 64 hops max, 40 byte packets

1  * * *
2  * * *
3  * * *
4  * * *

your firewall (whatever "hardware" means) probably block traceroute packets
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