Got a reply in the forums from "junovitch":

"There is a bug in 10.0-RELEASE with how how the kernel is tagging the mbuf 
allocated with IPSEC packets as it gets tagged to skip firewalling. Hence PF 
can't NAT what it can't see. Short answer is you need to upgrade to 10.0-STABLE 
or use an older version of FreeBSD.

Long answers:
http://www.freebsd.org/cgi/query-pr.cgi?pr=185876 - The PR with the technical 
details.
https://forums.freebsd.org/viewtopic.php?f=7&t=45691 - Same issue and the 
troubleshooting that helped find it."

Upgrading to 10 STABLE fixed the issue.

Cheers,
S.
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