To tackle the problem of training the careers of senior citizens numerous educational options may be attempted. However, the emerging complex puzzle of the diversity of training needs for the aforementioned trainee group, consisting of a mixture of formal and informal careers, calls for a careful and perhaps more radical than the usually attempted approach. To this extent, this paper describes elements of the innovative efforts followed upon the training design of the DISCOVER EU project. Specifically, simulations of virtual patients in Second Life are exploited in conjunction with educational components and objects in semantically extended e-learning environments, in an attempt to make more realistic everyday training cases and diverse topic, content rich approaches. The whole endeavor is presented in view of the existing limitations to elderly careers' training and is soon to lend itself to a rigorous pilot phase in Greece. Planned evaluation sessions are envisaged to certify successes, to inform for any required improvements but also to identify pitfalls.