The rise of non-fungible tokens (NFTs) has created new opportunities for investment in and management of art assets, yet painters entering this market require a combination of artistic, technological, and financial skills rarely addressed in Iranian art education. This study identifies the opportunities and challenges of such entry and proposes a testable analytical-decision framework for the smart financial management of tokenized painting assets. Using a descriptive-analytical approach grounded in purposive content analysis of 22 scholarly sources (2014-2026), the findings are synthesized into a testable conceptual model comprising five research propositions and a four-layer framework (asset, market, technology and smart contract, portfolio and risk). Two composite indices (Artist Readiness Score and Potential Liquidity Score) are combined into a Smart Entry Index (SEI). Additionally, a rule-based artificial intelligence model and Monte Carlo simulation for risk scenarios are introduced. Successful entry depends on combining artistic-visual, technological-blockchain, and digital-marketing skills. Liquidity and trading volume are the strongest price predictors, social-media activity correlates negatively with price, and superstar effects with herding behaviour dominate the market. Realized returns exhibit strong right skewness. An empirical illustration of the framework on a sample of five Iranian painters shows that the Smart Entry Index (SEI) reaches approximately 85.6 for the most active and liquid case (artist Ali Sabet), while Monte Carlo simulation shows that SEI-weighted portfolio diversification reduces the probability of loss from about 68% (concentrated portfolio) to about 24% (diversified portfolio). To account for Iran-specific contextual risks, an adjusted index, SEI_Iran, is introduced using a conservative discount coefficient (β ≈ 0.24). The proposed framework, operationalized through risk-adjusted return measures (adapted Sharpe ratio and RadaR) and three liquidity metrics, provides an operational tool for valuation and intelligent decision-making for Iranian artists and investors and advances smart financial management in digital assets.