The U.S.-based VitisGen project (www.vitisgen.org, funded by the USDA-NIFA SCRI award number 2011-51181-30635) unites grapevine breeding programs nationally to accelerate grapevine cultivar development via next generation DNA sequencing technology, and both local and centralized trait evaluation. To overcome the challenge of integrating relevant genetic resources, cutting-edge genotypic data, and robust phenotypes, our research team has employed a strategy that 1) maintains breeding germplasm locally, 2) collects and analyzes high-resolution genotypic data centrally, and 3) collects and analyzes phenotypic data both locally and in three phenotyping centers specializing in fruit chemistry, low temperature responses, and powdery mildew resistance. Locally, our research teams have phenotyped more than 100 unique traits ranging from disease resistance (such as downy mildew, black rot, and Phomopsis) to fruit quality attributes (such as berry skin color, berry diameter, and seedlessness). Here, we will share the unexpected challenges and opportunities derived from our experiences maintaining 17 core mapping families, genotyping 28,000 individuals, and collecting over a million phenotypic data points. We will also highlight new approaches developed to phenotype tannin extractability, disease resistance, and leaf morphology. These stories and results will facilitate cultivar improvement and help elucidate new strategies for improved trait evaluation.