I found out about a customer of Small Tree's having a problem like this last week. They had several ports on one subnet.
I always warn people not to do this because the way BSD routing works, there will only be one route to all of the subnets. So outbound traffic will all be flowing out of one port. (You could verify this by running "sar -n DEV 2 100" in a terminal)
If you must have more bandwidth on one network, use link aggregation. That will give you the bandwidth and a single IP address on the subnet.
If you have some kind of broadcast/redundant internet broadband thing going on, then use a private vlan giving each port access to the world in such a way that they can't hear each other. (Classrooms do this sort of thing for guest networks). It doesn't solve the single route issue, but it could work for outbound stuff.
Apple must have changed something in their OS X piracy checking that causes problems when the other ports "hear" the server coming from the one port broadcasting.
If you absolutely have to do something like this, then talk to Peter Sichel over at Sustainable Softworks. He's got an inexpensive routing package that can "source route". This forces responses to go back over the same port the original socket came in on. I don't know if it'll solve the OS X licensing issue, but it can make sure you see outbound traffic on all ports as is supposed to happen.