> I think you're underestimating the extent to which homophones are prevalent in Chinese. It's not just classical texts, it's all written texts and most non-trivial spoken words, including names. The vast majority of Chinese morphemes are only a syllable long, and have up to hundreds of homophones.

I guess my question is how much of a problem are these in spoken communication (say over a telephone where there's less shared situational context)? My intuition is that if the prevalence of homophones were so troublesome to make a phonetic writing system difficult/impractical to use, they'd also make spoken telephone conversations similarly difficult/impractical. Since Chinese people can obviously speak productively on the telephone, then there must be enough context in the phoneme-stream that it's sufficient to effectively communicate without the extra context provided by the characters.

That's not to say the characters don't provide an extra layer of depth and subtlety to written text over phonetic writing.