Diagrammatic many-body theory is used to calculate the scattering phase shifts, normalized annihilation rates ${Z}_{\mathrm{eff}}$, and annihilation $\ensuremath{\gamma}$ spectra for positron collisions with the hydrogenlike ions He${}^{+}$, Li${}^{2+}$, B${}^{4+}$, and F${}^{8+}$. Short-range electron-positron correlations and longer-range positron-ion correlations are accounted for by evaluating nonlocal corrections to the annihilation vertex and the exact positron self-energy. The numerical calculation of the many-body theory diagrams is performed using $B$-spline basis sets. To elucidate the role of the positron-ion repulsion, the annihilation rate is also estimated analytically in the Coulomb-Born approximation. It is found that the energy dependence and magnitude of ${Z}_{\mathrm{eff}}$ are governed by the Gamow factor that characterizes the suppression of the positron wave function near the ion. For all of the H-like ions, the correlation enhancement of the annihilation rate is found to be predominantly due to corrections to the annihilation vertex, while the corrections to the positron wave function play only a minor role. Results of the calculations for $s$-, $p$-, and $d$-wave incident positrons of energies up to the positronium-formation threshold are presented. Where comparison is possible, our values are in excellent agreement with the results obtained using other, e.g., variational, methods. The annihilation-vertex enhancement factors obtained in the present calculations are found to scale approximately as $1+(1.6+0.46\ensuremath{\ell})/{Z}_{i}$, where ${Z}_{i}$ is the net charge of the ion and $\ensuremath{\ell}$ is the positron orbital angular momentum. Our results for positron annihilation in H-like ions provide insights into the problem of positron annihilation with core electrons in atoms and condensed matter systems, which have similar binding energies.