Self-supervised learning (SSL) is increasingly used in medical imaging to reduce annotation requirements, but representation quality is often judged using a single downstream evaluation setting. For dense clinical tasks, this can confound representation quality with the capacity of the downstream model used to recover task-relevant information. We present a systematic evaluation of self-supervised representations for left-ventricular segmentation and ejection fraction (EF) estimation from apical four-chamber echocardiography on EchoNet-Dynamic. Rather than relying on a single downstream probe, we compare a hierarchy of extraction strategies with increasing expressivity: heuristic extraction without mask-supervised training, frozen linear probes, frozen lightweight decoder probes, and partial fine-tuning. We apply this framework to two complementary representation families: generic frozen self-DIstillation with NO labels (DINOv3) features and a task-adapted dense self-supervised representation, Bootstrap Your Own Segmentation (BYOS). In both families, heuristic extraction substantially understated what was recoverable from the frozen representation. For DINOv3, performance improved from Dice 0.684 and EF mean absolute error (MAE) 13.01 under heuristic extraction to Dice 0.906 and EF MAE 9.65 with a frozen lightweight decoder, approaching a supervised U-Net baseline (Dice 0.915, EF MAE 9.72). For BYOS, performance improved from Dice 0.687 and EF MAE 17.83 under heuristic extraction to Dice 0.902 and EF MAE 8.74 with a frozen lightweight decoder. These results show that conclusions about self-supervised representation quality in dense echocardiographic analysis depend strongly on the downstream extraction strategy used for evaluation. We therefore argue that multi-strategy evaluation is an important methodological consideration for SSL in dense medical image analysis.

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