In addition to their jet-like dynamic behaviour, spicules usually exhibit strong transverse speeds, multi-stranded structure and heating from chromospheric to transition region temperatures. In this work we first analyse Hinode & IRIS observations of spicules and find different behaviours in terms of their Doppler velocity evolution and collective motion of their sub-structure. Some have a Doppler shift sign change that is rather fixed along the spicule axis, and lack coherence in the oscillatory motion of strand-like structure, matching rotation models or long wavelength torsional Alfvén waves. Others exhibit a Doppler shift sign change at maximum displacement and coherent motion of their strands, suggesting a collective MHD wave. By comparing with an idealised 3D MHD simulation combined with radiative transfer modelling, we analyse the role of transverse MHD waves and associated instabilities in spicule-like features. We find that Transverse Wave Induced Kelvin-Helmholtz (TWIKH) rolls lead to coherence of strand-like structure in imaging and spectral maps, as seen in some observations. The rapid transverse dynamics and the density and temperature gradients at the spicule boundary lead to ring-shaped Mg II k and Ca II H source functions in the transverse cross-section, potentially allowing IRIS to capture the KHI dynamics. Twists and currents propagate along the spicule at Alfvénic speeds, and the temperature variations within TWIKH rolls produce sudden appearance/disappearance of strands seen in Doppler velocity and in Ca II H intensity. However, only a mild intensity increase in higher temperature lines is obtained, suggesting there is an additional heating mechanism at work in spicules.