I have been encountering a bit of trouble getting a fileserver to
establish a vpn to my local network. I do not have access to the
machines at the moment, so my first question is this - do both
machines need to have incoming access to ports 500/4500? I am trying
to make the fileserver in question act somewhat like a roadwarrior
(although NAT-T should not be needed) in the sense that it is
firewalled off.

pf.conf should be irrelevant, as I have added "set skip on enc0" and
"pass quick on $ext_if from x.x.x.x".

Neither the network B gateway nor network B hosts are able to ping the
fileserver and vice versa. Also, ipsecctl -sa shows normal SAD and
FLOWS - so it doesn't seem to be a problem with establishing the
connection.

Here is the information I have at the moment. More to come if needed.

Fileserver: 1.2.3.4 (no incoming ports allowed, but not behind NAT)
Network B Gateway: 5.6.7.8
Network B: 192.168.1.0/24

Fileserver ipsec.conf:
ike esp from 1.2.3.4 to 192.168.1.0/24 peer 5.6.7.8 psk password
ike esp from 1.2.3.4 to 5.6.7.8 psk password

Network B Gateway ipsec.conf:
ike passive esp from 192.168.1.0/24 to 1.2.3.4 psk password
ike passive esp from 5.6.7.8 to 1.2.3.4 psk password

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