The counterintuitive properties of photonic crystals, such as all-angle negative refraction (AANR) [J. Mod. Opt.34, 1589 (1987)] and high-directivity via ultrarefraction [Phys. Rev. Lett.89, 213902 (2002)], as well as localized defect modes, are known to be associated with anomalous dispersion near the edge of stop bands. We explore the implications of an asymptotic approach to uncover the underlying structure behind these phenomena. Conventional homogenization is widely assumed to be ineffective for modeling photonic crystals as it is limited to low frequencies when the wavelength is long relative to the microstructural length scales. Here a recently developed high-frequency homogenization (HFH) theory [Proc. R. Soc. Lond. A466, 2341 (2010)] is used to generate effective partial differential equations on a macroscale, which have the microscale embedded within them through averaged quantities, for checkerboard media. For physical applications, ultrarefraction is well described by an equivalent homogeneous medium with an effective refractive index given by the HFH procedure, the decay behavior of localized defect modes is characterized completely, and frequencies at which AANR occurs are all determined analytically. We illustrate our findings numerically with a finite-size checkerboard using finite elements, and we emphasize that conventional effective medium theory cannot handle such high frequencies. Finally, we look at light confinement effects in finite-size checkerboards behaving as open resonators when the condition for AANR is met [J. Phys. Condens. Matter 15, 6345 (2003)].