The point of the discussion was not to compare the 53E to the V-22. It was to establish a baseline for helicopter design. A similar comparison could have been made with a fixed wing aircraft. in terms of wing loading. Once again the V-22 would not fare very well. I do not have any specific issues with the V-22 only that it is stuck in the middle with an insufficient rotor to be a decent helicopter and not enough wing to be a decent transport airplane.
Speed was not specifically addressed as was HOGE. Either number would be skewed to a specific machine. To specifically answer the 250 KIAS H-53 question, the answer is most likely never. But I did fly an H-53E at 194 KIAS in straight and level flight as part of a demonstration sanctioned by the USN to verify what speed may be attainable in a future medium lift helicopter. 194 KIAS was achieved without exceeding airframe or engine limitations. Only the Vne was exceeded. That would make up 50% of the V-22 advantage.