Creative micro, small, and medium enterprises (MSMEs) require digital transformation strategies that fit their heterogeneous capabilities, yet many assistance programs still provide generic recommendations. This paper proposes and tests an explainable hybrid decision support approach for selecting digital transformation strategies in creative MSMEs. The method combines subjective weights obtained from expert-oriented fuzzy multi-criteria reasoning, objective weights computed by CRITIC, MARCOS-based strategy ranking, and machine learning classification for adaptive readiness prediction. A controlled synthetic dataset of 120 MSMEs with eleven digital-readiness criteria was generated to demonstrate the complete computational procedure without claiming field-level impact. The hybrid weighting produced dominant priorities for digital content capability, digital literacy, social media use, marketplace adoption, and technology readiness. MARCOS ranking indicated that digital branding, content marketing, and creative community collaboration were the highest priority strategies. Machine learning evaluation using a 75:25 train-test split showed that the best classifier achieved an accuracy of 0.97 and a macro F1-score of 0.96. Permutation-based explainability identified digital literacy, digital content capability, and marketplace adoption as influential predictors. The results demonstrate that the proposed approach can produce transparent and auditable recommendations for MSME digitalization research. Keywords: Decision Support System; Digital Transformation; Explainable AI; Fuzzy MCDM; MSME