Cognitive impairments are among the most common age-related disabilities worldwide. Literature has shown that cognitive training using Virtual Reality (VR) systems can be a valid and effective solution for cognitive rehabilitation. Virtual environments can be easily customized to deliver very specific training by controlling the presentation of stimuli and keeping track of the user responses. Reh@City (RC) is a virtual reality simulation of a city where patients can train a variety of cognitive skills while performing simulated activities of daily living. An initial prototype of this city with four environments was clinically validated with a stroke sample, and the encouraging results motivated further iterations and improvements in the RC, in terms of its tasks, interaction with the content, and task adaptation. This paper presents the efforts of creating RC v2.0, a VR-based software system for cognitive rehabilitation that presents different cognitive training tasks that take place in 8 realistically modeled 3D environments, that are personalized to the patient clinical profile and also implements automatic difficulty adaptation.