Sentiment Analysis, also known as Opinion Mining, gained prominence in the early 2000s alongside the emergence of internet forums, blogs, and social media platforms. Researchers and businesses recognized the imperative to automate the extraction of valuable insights from the vast pool of textual data generated online. Its utility in the business domain is undeniable, offering actionable insights into customer opinions and attitudes, empowering data-driven decisions that enhance products, services, and customer satisfaction. The expansion of Sentiment Analysis into the financial sector came as a direct consequence, prompting the adaptation of powerful Natural Language Processing models to these contexts. In this study, we rigorously test numerous classical Machine Learning classification algorithms and ensembles against five contemporary Deep Learning Pre-Trained models, like BERT, RoBERTa, and three variants of FinBERT. However, its aim extends beyond evaluating the performance of modern methods, especially those designed for financial tasks, to a comparison of them with classical ones. We also explore how different text representation and data augmentation techniques impact classification outcomes when classical methods are employed. The study yields a wealth of intriguing results, which are thoroughly discussed.