IEEE 802.11ah is a novel sub-GHz license-free WiFi technology that is of great interest for Smart Cities, primarily due to its long range, low energy consumption, reliability, and ubiquitousness. To guarantee a long lifetime of battery-powered IEEE 802.ah Mobile Terminals (MTs), network discovery-based on beaconing and probing should ideally be avoided. Alternative discovery approaches heavily rely on crowd-sourcing, which in turn relies on propagation modeling. Due to the novelty of IEEE 802.11ah, the accuracy of the available propagation models is currently all but clear, and this paper makes one of the first steps in bridging this gap. Specifically, for a number of Smart City-relevant environments we experimentally evaluate the accuracy of an exhaustive set of models by comparing their outputs against real measurements obtained using IEEE 802.11ahcompatible hardware. Our results are encouraging, showing that the existing models are indeed suitable for IEEE 802.11ah. However, they also indicate that diverse models perform best in distinct types of deployment environment, suggesting the need for an environment-tailored design of IEEE 802.11ah-based systems that use propagation modeling.