The Universe on scales 10 - 100/h Mpc is dominated by a cosmic web of voids, filaments, sheets and knots of galaxy clusters. These structures participate differently in the global expansion of the Universe: from non-expanding clusters to the above average expansion rate of voids. In this paper we characterize Hubble expansion anisotropies in the COMPOSITE sample of 4534 galaxies and clusters. We concentrate on the dipole and quadrupole in the rest frame of the Local Group. These both have statistically significant amplitudes. These anisotropies, and their redshift dependence, cannot be explained solely by a boost of the Local Group in the Friedmann-Lemaître-Robertson-Walker (FLRW) model which expands isotropically in the rest frame of the cosmic microwave background (CMB) radiation. We simulate the local expansion of the Universe with inhomogeneous Szekeres models, which match the standard FLRW model on > 100/h Mpc scales but exhibit nonkinematic relativistic differential expansion on small scales. We restrict models to be consistent with observed CMB temperature anisotropies, while simultaneously fitting the redshift variation of the Hubble expansion dipole. We include features to account for both the Local Void and the ``Great Attractor''. While this naturally accounts for the Hubble expansion and CMB dipoles, the simulated quadrupoles are smaller than observed. Further refinement to incorporate additional structures may improve this. This would enable a test of the hypothesis that some large angle CMB anomalies result from failing to treat the relativistic differential expansion of the background geometry; a natural feature of solutions to Einstein's equations not included in the current standard model of cosmology.