Apparatus and associated methods that allow a user (e.g., cable or satellite network subscriber) to access content, such as a video program, from a location outside the subscriber's network, with dynamic or adaptive insertion of secondary content (e.g., advertisements or promotions) that are more relevant for that context. In one embodiment, a personal content server streams the content to the subscriber over a network connection from the local e.g., (subscription) network to a remote network upon authorization by a content manager process; secondary content is evaluated and selectively inserted or replaced depending on factors such as the user's remote location, the configuration of their platform, the date and time of their access request, and/or the subject matter of the primary content.