In this paper, we present Howdy Y’all, a multi-modal task-oriented dialogue agent developed for the 2021-2022 Alexa Prize TaskBot competition. Our design principles guiding Howdy Y’all aim for high user satisfaction through friendly and trustworthy encounters, minimization of negative conversation edge cases, and wide coverage over many tasks. Hence, Howdy Y’all is built upon a rapid prototyping platform to enable fast experimentation and powered by four key innovations to enable this vision: (i) First, it combines a rules, phonetic matching, and a transformer-based approach for robust intent understanding. (ii) Second, to accurately elicit user preferences and guide users to the right task, Howdy Y’all is powered by a contrastive learning search framework over sentence embeddings and a conversational recommender for eliciting preferences. (iii) Third, to support a variety of user question types, it introduces a new data augmentation method for question generation and a self-supervised answer selection approach for improving question answering. (iv) Finally, to help motivate our users and keep them engaged, we design an emotional conversation tracker that provides empathetic responses to keep users engaged and a monitor of conversation quality.