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Interesting discussion. Maybe this has already been mentioned, but it seems to me that the optimal solution would be the same lobby in *The Shadow of Death* as in *Heroes of Might and Magic III: The Restoration of Erathia*, but as optional paid functionality.
Playing *Heroes 3* through GameRanger and Hamachi is not very convenient; a lobby would allow attracting completely casual players, in the spirit of playing against a friend while having a beer and some squid. For these people, *Online Battles* are completely unnecessary, because they play once a month, and the thought of paying for a popular game will cause confusion.
Experienced players, on the other hand, will pay and enjoy playing in their own environment.