You misunderstand how Dreambox-based sharing works. Cardsharing is about sharing decryption codes with remote clients, each of which has his own dish and tuner. In that situation each client can watch his own program independently of the others.
What you are doing is streaming. Your DM500 has only one tuner which means it cannot receive more than one transponder frequency at once. Typically the channel you want to watch will be on a different frequency to the one your friend is watching, which means simultaneous reception of those channels on the one tuner is impossible. The enigma web interface is designed for remote control of a box, and though the box can stream its tuned channel out to a client it can't stream different channels simultaneously. You're thinking of web streaming servers that provide different content to many clients simultaneously, but those servers are large and expensive - unlike the DM500 which has barely enough processing power and bandwidth for a single user.
To do what you want you'd need to set up a dish for your receiver and tune using your own receiver's tuner, not using the web interface of the other box (which has its own dish and tuner). The network between your friend and you wouldn't be carrying pictures, only bursts of decryption keys every ten seconds or so. That means your friend would be running a cardsharing server on his box, such as NewCS, and you'd be running a cardsharing client such as mgcamd or evocamd. Architecturally that's how it works. Sharing the subscription between different households is a breach of the contract so I won't be any more specific than that. Setting up networks like that between different rooms of a home, for personal use, is OK though.
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