Research in bioacoustics, neuroscience, and linguistics often uses birdsong as a proxy to acquire knowledge across diverse areas. This requires audio models to annotate and parse the birdsong. Developing such models requires precise, syllable-level annotated training data. Therefore, automated methods that reduce annotation costs are in demand. This work presents a data-efficient birdsong annotator called Residual Multi-Layer Perceptron Recurrent Neural Network. It then presents a three-stage training pipeline for developing reliable birdsong syllable detectors with minimal annotation. The first stage is self-supervised learning from unlabeled data. Two of the most successful pretraining paradigms are explored, namely, masked prediction and online clustering. The second stage is supervised training with effective data augmentation to produce a robust frame-level syllable detector for each individual. The third stage is a semi-supervised post-training step that refines each individual's model using unlabeled data. The effectiveness of this approach is demonstrated for the Canary song in extreme label-scarcity scenarios. From a signal-processing perspective, the Canary song exhibits one of the most challenging spectro-temporal patterns for algorithmic time-series annotation: rapid vocalizations, brief inter-syllabic intervals, fast and broadband frequency sweeps, and spectrally similar syllables that require fine-grained features to distinguish. Hence, a successful syllable detection algorithm for Canary also establishes a robust baseline for other birds. This methodological generalization is validated in a case study of Bengalese Finch song annotation. Finally, the potential of self-supervised embeddings is assessed for linear probing and unsupervised birdsong analysis.