Why so many definitions associated with each word?
Chinese was once monosyllabic, where one character represented one word. But back then, thousands of years ago, pronunciation for characters was also much more distinct, and still is in certain topolects (like Cantonese).

Modern Mandarin, on the other hand, compensates for lack of precision in pronunciation by being polysyllabic, where mosts words are either disyllabic or trisyllabic. There are still monosyllabic words, but they are usually easily comprehensible by context (like 我 and other pronouns).

Most of the characters you list are rather rare, biut let’s consider the common ones. 奖 (獎), as in prize, award, is usually found in compounds such as Nuobei’erjiang (Nobel prize), jiangjin (money award), jiangpai (prize medal) and so on.

This could hardly be confused with 讲, speak, with compounds such as jiangjia (bargain), jianghua (talk), jiangjie (explain) and so on.

We could also refer to 蒋介石 (Jiang Jieshi), where 蒋 is a common family name. Context will mostly be evident when names are invoked.

Your strategy should therefore be to learn compound words. Since you do not want to learn written Chinese, just forget that there are characters, there are only words, and words are usually polysyllabic: women, gongneng, guangchang, gonggong qiche, laobanniang, dalu, mantou, chengyu, and so on.