If you've quadruple checked all the settings and confirmed the server and clients are using the same ports and the web admin interface is using a different port, I'd say stick a packet sniffer (such as Ethereal) on the server and a client and confirm the client is attempting to connect and the server is seeing the packets and work from there. I'd also probably hook the client to the same switch as the server while troubleshooting.
Issuing "wuauclt /detectnow" and "gpupdate /force" on the client can hasten the detection process, otherwise you'll have to wait until the client lazily decides to check for updates, and then updates itself if necessary. The default time period is 22 hours I think.
Another problem can be if you imaged the clients without sysprepping, they will all appear as a single client. See
WSUS - Client Configuration Checks & Known Issues for resolution and other tips.