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Even when I think I've memorized how to read a particular kanji, 人 (ひと) for example, and try to read other words I find that it's also pronounced じん...and I'm sure it probably has many other readings.
Should readings just be taken on a case-by-case basis / word-by-word basis? Is there any point to memorizing a single kanji reading and applying it else where or is there some structure to when each reading is used?
Most of the time, kanji are used to write words or parts of words—prefixes, suffixes, and so on. To know which reading is appropriate, you have to know the relevant Japanese words or parts of words.
For example, look at the following:
にほんじん 'Japanese person/people'
アメリカじん 'American(s)'
がいこくじん 'foreigner(s)'
Here, we have a suffix じん meaning "person". As you can see, it attaches to nouns that denote places people are from. That's not the only way じん can be used, but it's a pattern you need to learn. And once you know this pattern, you can read the following:
日本人 にほんじん (not *にほんにん)
アメリカ人 アメリカじん (not *アメリカにん)
外国人 がいこくじん (not *がいこくにん)
There are two ways you can learn this sort of pattern:
Implicitly: You can learn words like the above and read new words by analogy:
Hmm, what's this word? It says フランス人, but I haven't learned that word yet, so how do I know which reading to use? Well, I know the words 日本人 and アメリカ人, and it's じん in both of those. I bet this word is フランスじん!
You'll probably do a combination of both as you learn. When you do, you'll be learning facts about the Japanese language—not just about kanji or readings, but about how words and parts of words fit together and what they mean when they do.
There are certain overarching patterns you'll notice pretty early on in your studies, and you can fall back on these patterns when you aren't sure:
These rules are far from absolute! Although most compounds are kun-kun or on-on, mixed compounds (called 重箱読み and 湯桶読み) are still relatively common—much like how in English, we have hybrids like television (Greek-Latin) and biathlon (Latin-Greek).
And there are overriding factors:
Some words or parts of words are productive, meaning they form new words or compounds readily. Our example of じん above is very productive; you can invent a place name and combine it with that name, if you like. Others are less productive, or not productive at all. For example, 一人 is ひとり, but り only appears in a very small set of words that you'll have to memorize. You can't form new words with it yourself.
Occasionally words are suppletive, meaning they take the place of an expected form. Although にん as a counter for people is very productive, the suppletive words ひとり and ふたり generally take the place of the expected forms いちにん and ににん. You have to memorize these words as exceptions.
Sometimes different readings have different meanings. For example, 塞 has two on readings, そく and さい. The former is used when it means ふさぐ 'obstruct', and the latter when it means とりで 'fortress'.
So you can't simply memorize a set of readings for each kanji, I'm afraid. You'll have to learn Japanese words and parts of words, to learn how those are written, and to make educated guesses based on what you've learned so far when your knowledge falls short.
Both strategies have their place, depending on which set of readings you're studying at a given time.
When you're studying 音読み【おんよみ】(the Chinese-derived readings), it's best to learn the sound first, and then learn a couple of words that use it with each reading so that you can get a sense of when it's used.
To use your 人 example, learn that it's pronounced じん, then find words that use じん—things like 日本人【にほんじん】 and 人類【じんるい】. Then move on to the next reading (にん) and do the same: 人間【にんげん】、上人【じょうにん】, etc. The words don't have to be exotic; as a matter of fact, picking ones that you commonly use is ideal when possible.
The great thing about this strategy is that it enables you to make educated guesses at new words if you haven't seen them before, but know the character's meanings and probable readings. You won't always get it right on the first try, but the skill refines itself over time and practice.
One of the biggest mistakes I made with 訓読み【くんよみ】(native Japanese readings) was to start out learning many of them as just readings, devoid of distinct meaning. Let's take an example:
見：み・る、み・える、み・せる
The character 見 has a collection of general meanings regarding vision ("look", "see", etc.). But if all you know about it is that it has to do with seeing and you have 3 possible verbs to use, how do you tell which one?
In cases like this, it's best to suck it up and put in a bit of extra effort to learn the actual meanings of the words associated with the readings. In this case:
As you can see (forgive the pun), the general meaning of "see" isn't completely off the mark, but the choice of which verb to use depends on which dimension of that meaning you're trying to convey.
Another thing to be aware of is that sometimes some 訓読み are more commonly used in conjunction with something else, instead of as standalone words. Moving back to your 人 example, we have the following:
人：ひと、り、と
In this case, 人【ひと】 can stand on its own, meaning "person". The other two mean "person" as well, but in slightly different contexts:
Just because a reading is listed under a kanji doesn't necessarily mean you're going to find many examples of it out in the wild, especially as a foreigner. 生 famously has about 20 readings, but many of them (such as な・す、む・す、and お・う) really don't come up often, while others overlap with contextually more specific characters (活ける【いける】、産む【うむ】). Likewise, KANJIDIC (which is the source of most free online kanji dictionaries) has occasional errors or archaic/hard-to-find readings (e.g. it lists 二び【ふたたび】, which is a valid reading, but rather obscure).
In short, if you're having trouble finding examples of a reading in use, don't stress over it; move on to the next one on the list or ask a native speaker to help provide you with an example.
