Monitoring and understanding forest dynamics is essential for environmental conservation and management. This is why the Swiss National Forest Inventory (NFI) provides countrywide vegetation height maps at a spatial resolution of 0.5 m. Its long update time of 6 years, however, limits the temporal analysis of forest dynamics. This can be improved by using spaceborne remote sensing and deep learning to generate large-scale vegetation height maps in a cost-effective way. In this paper, we present an in-depth analysis of these methods for operational application in Switzerland. We generate annual, countrywide vegetation height maps at a 10-m ground sampling distance for the years 2017–2020 based on Sentinel-2 satellite imagery. In comparison to previous works, we conduct a large-scale and detailed stratified analysis against a precise Airborne Laser Scanning reference dataset. This stratified analysis reveals a close relationship between the model accuracy and the topology, especially slope and aspect. We assess the potential of deep learning-derived height maps for change detection and find that these maps can indicate changes as small as 250 m². Larger-scale changes caused by a winter storm are detected with an F1-score of 0.77. Our results demonstrate that vegetation height maps computed from satellite imagery with deep learning are a valuable, complementary, cost-effective source of evidence to increase the temporal resolution for national forest assessments.