Bridges are vital assets of transport infrastructure, systems, and communities. Damage characterization is critical in ensuring safety and planning adaptation measures. Nondestructive methods offer an efficient means towards assessing the condition of bridges, without causing harm or disruption to transport services, and these can deploy measurable evidence of bridge deterioration, e.g., deflections due to tendon loss. This paper presents an enhanced input-doubling technique and the Artificial Neural Network (ANN)-based cascade ensemble method for bridge damage state identification and is exclusively relying on small datasets, that are common in structural assessments. A new data augmentation scheme rooted in the principles of linearizing response surfaces is introduced, which significantly boosts the efficiency of intelligent data analysis when faced with limited volumes of data. Furthermore, improvements to a two-step ANN-based ensemble method, designed for solving the stated task, are presented. By adding the improved input-doubling methods as simple predictors in the first part of the cascade ensemble and optimizing it, we significantly boost accuracy (7%, 0.5%, and 8% based on R2 in predicting tendon losses for three critical zones that were defined across the deck of a real deteriorated prestressed balanced cantilever bridge). This improvement is strong evidence of the accuracy of the proposed method for the task at hand that is proven to be more accurate than other methods available in the international literature.