This paper explores transformer-based models for music overpainting, focusing on jazz piano variations. Music overpainting generates new variations while preserving the melodic and harmonic structure of the input. Existing approaches are limited by small datasets, restricting scalability and diversity. We introduce VAR4000, a subset of a larger dataset for jazz piano performances, consisting of 4,352 training pairs. Using a semi-automatic pipeline, we evaluate two transformer configurations on VAR4000, comparing their performance with the smaller JAZZVAR dataset. Preliminary results show promising improvements in generalisation and performance with the larger dataset configuration, highlighting the potential of transformer models to scale effectively for music overpainting on larger and more diverse datasets.