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Skype has significant problems with multiple users and video quality. Skype recommends that a max of 5 users group chat as video quality is severely affected. Even webcams tested with other chat services showed lower quality when used with Skype. See More
Messages are sent and received only when both ends are online, if neither end is using a cloud-enabled device. In this case, if you are online 9-17 and your recipient is online 18-3, messages will never be delivered. See More