We present a scheme for modeling HF radio signal characteristics along paths of different lengths, which is based on the waveguide approach — the normal mode method. We use a representation of the recorded signal field in the form of Green function products of the angular operator, excitation coefficients, and reception coefficients of individual normal modes. Algorithms have been developed for calculating distance-frequency, frequency-angular, and amplitude characteristics of signals in large spatial regions through analysis and numerical summation of normal mode series. We have implemented a complex algorithm for simulating propagation conditions of HF radio signals, which includes a medium model, algorithms for calculating signal characteristics, and operational diagnostics of radio channel. We have compared the results of the HF signal propagation characteristic modeling and the experimental oblique sounding data obtained along paths of different lengths and orientation. To analyze experimental ionograms, determine the maximum usable frequencies for propagation modes along radio paths, we employ the method of automatic processing and interpretation of oblique sounding ionograms.