Timely availability of images of suitable spatial resolution, temporal frequency and coverage is currently one of the major technical constraints on the application of satellite SAR remote sensing for the conservation of heritage assets in urban environments that are impacted by human-induced transformation. TerraSAR-X and Sentinel-1A, in this regard, are two different models of SAR data provision: very high resolution on-demand imagery with end user-selected acquisition parameters, on one side, and freely accessible GIS-ready products with intended regular temporal coverage, on the other. What this means for change detection analyses in urban areas is demonstrated in this paper via the experiment over Homs, the third largest city of Syria with an history of settlement since 2300 BCE, where the impacts of the recent civil war combine with pre- and post-conflict urban transformation . The potential performance of Sentinel-1A StripMap scenes acquired in an emergency context is simulated via the matching StripMap beam mode offered by TerraSAR-X. Benefits and limitations of the different radar frequency band, spatial resolution and single/multi-channel polarization are discussed, as a proof-of-concept of regular monitoring currently achievable with space-borne SAR in historic urban settings. Urban transformation observed across Homs in 2009, 2014 and 2015 shows the impact of the Syrian conflict on the cityscape and proves that operator-driven interpretation is required to understand the complexity of multiple and overlapping urban changes.