Both netmasks will work but it's common to use 255.255.255.255 when the jail IP is an alias of the hosts interface. The IP addresses don't appear to be the problem though. "No address record" always indicates DNS or resolving issues. Check your jail's /etc/resolv.conf, make sure there's at least one valid DNS server.
As drill(1) does seem to work make sure your repositories are set correctly. Check with
The re0 interface can safely be ignored. Although it's loaded it's not actually active (status: no carrier) so it's not interfering with anything.
As drill(1) does seem to work make sure your repositories are set correctly. Check with
pkg -vv
to see if the URL is correct (it may point to a non-existing hostname). I'd also verify if HTTP_PROXY and friends aren't the cause.The re0 interface can safely be ignored. Although it's loaded it's not actually active (status: no carrier) so it's not interfering with anything.