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Training deep learning models requires having the right data for the problem and understanding both your data and the models’ performance on that data. Training deep learning models is difficult when data are limited, so in this paper, we seek to answer the following question: how can we train a deep learning model to increase its performance on a targeted area with limited data? We do this by applying rotation data augmentations to a simulated synthetic aperture radar (SAR) image dataset. We use the Uniform Manifold Approximation and Projection (UMAP) dimensionality reduction technique to understand the effects of augmentations on the data in latent space. Using this latent space representation, we can understand the data and choose specific training samples aimed at boosting model performance in targeted under-performing regions without the need to increase training set sizes. Results show that using latent space to choose training data significantly improves model performance in some cases; however, there are other cases where no improvements are made. We show that linking patterns in latent space is a possible predictor of model performance, but results require some experimentation and domain knowledge to determine the best options.