In light of recent privacy regulations, machine unlearning has attracted significant attention in the research community. However, current studies predominantly assess the overall success of unlearning approaches, overlooking the varying difficulty of unlearning individual training samples. As a result, the broader feasibility of machine unlearning remains under-explored. This paper presents a set of novel metrics for quantifying the difficulty of unlearning by jointly considering the properties of target model and data distribution. Specifically, we propose several heuristics to assess the conditions necessary for a successful unlearning operation, examine the variations in unlearning difficulty across different training samples, and present a ranking mechanism to identify the most challenging samples to unlearn. We highlight the effectiveness of the Kernelized Stein Discrepancy (KSD), a parameterized kernel function tailored to each model and dataset, as a heuristic for evaluating unlearning difficulty. Our approach is validated through multiple classification tasks and established machine unlearning algorithms, demonstrating the practical feasibility of unlearning operations across diverse scenarios.