Radio Frequency Machine Learning (RFML) is the application of ML techniques to solve problems in the RF domain as an alternative to traditional digital-signal processing (DSP) techniques. Notable among these are the tasks of specific emitter identification (SEI), determining source identity of a received RF signal, and automated modulation classification (AMC), determining the modulation scheme of a received RF transmission. Both tasks have a number of algorithms that are effective on simulated data, but struggle to generalize to data collected in the real-world, partially due to the lack of available datasets upon which to train models and understand their limitations. This thesis covers the practical considerations for systems that can create high-quality datasets for RFML tasks, how variances from real-world effects in these datasets affect RFML algorithm performance, and how well models developed from these datasets are able to generalize and adapt across different receiver hardware platforms. Moreover, this thesis presents a proof-of-concept system for large-scale and efficient data generation, proven through the design and implementation of a custom platform capable of coordinating transmissions from nearly a hundred Software-Defined Radios (SDRs). This platform was used to rapidly perform experiments in both RFML performance sensitivity analysis and successful transfer between SDRs of trained models for both SEI and AMC algorithms. / Master of Science / Radio Frequency Machine Learning (RFML) is the application of machine learning techniques to solve problems having to do with radio signals as an alternative to traditional signal processing techniques. Notable among these are the tasks of specific emitter identification (SEI), determining source identity of a received signal, and automated modulation classification (AMC), determining the data encoding format of a received RF transmission. Both tasks have practical limitations related to the real-world collection of RF training data. This thesis presents a proof-of-concept for large-scale, efficient data generation and management, as proven through the design and construction of a custom platform capable of coordinating transmissions from nearly a hundred radios. This platform was used to rapidly perform experiments in both RFML performance sensitivity analysis and successful cross-radio transfer of trained behaviors.