This paper proposes a dual-engine AI architectural method designed to address the complex problem of exploring potential trajectories in the evolution of art. We present two interconnected components: AIDA (an artificial artist social network) and the Ismism Machine, a system for critical analysis. The core innovation lies in leveraging deep learning and multi-agent collaboration to enable multidimensional simulations of art historical developments and conceptual innovation patterns. The framework explores a shift from traditional unidirectional critique toward an intelligent, interactive mode of reflexive practice. We are currently applying this method in experimental studies on contemporary art concepts. This study introduces a general methodology based on AI-driven critical loops, offering new possibilities for computational analysis of art.