This study proposes an AI-assisted guiding model for integrating photographic place criteria into digital place making processes in urban landscape revitalization. Building on theories of environmental perception, imageability, and landscape aesthetics, the study conceptualizes Instagrammability not as a transient cultural trend but as a perceptual-aesthetic indicator grounded in spatial qualities. Photographic place criteria were derived from the literature and tested through a CLIP-based multilabel image-text analysis using images of globally Instagrammed urban landscapes. The validated criteria were subsequently applied to a former industrial heritage site, the Pasabahce Glass Factory in Istanbul, using DALL·E based generative image editing to produce multiple design alternatives. The results demonstrate that recurrent spatial qualities such as geometric clarity, lighting, dominant patterns, and architectural distinctiveness significantly enhance photographability. The proposed model guides designers and planners in digital placemaking processes while emphasizing ethical considerations, participatory integration, and spatial sustainability.