This work presents the lessons learned and critical updates to the Research Oriented Underwater Glider for Hands-on Investigative Engineering (ROUGHIE). The open water testing experience with the original ROUGHIE provides key insight to design and operation of small scale autonomous underwater vehicles. This paper is organized to share necessary considerations that will be crucial for future vehicle developments. It also describes ROUGHIE 2.0 design updates that include performance, reliability, and ease-of-use improvements. Due to the modular design of the ROUGHIE, each module was able to be upgraded as an independent system. The integrative system performance is then analyzed through exhaustive experimentation in controlled environments to prepare the ROUGHIE 2.0 for open-water deployments. The upgrades improve the ROUGHIE's functionality as a robust and user-friendly undersea scientific research infrastructure.