Learning strategies for WK's arbitrary system of drilling readings?

[rfindley]

Yep, exactly. I wrote the following a while back to help new users understand:

How do you know when to use the right reading?

In daily usage, vocabulary is the only reading that matters. It’s what you’ll see on a sign, or in a restaurant menu, or in a novel that you’re reading. A word is (usually) only pronounced one way. But the same kanji in a different word may be pronounced differently. To illustrate with English, the words ‘cat’ and ‘civil’ are each only pronounced one way. But notice that ‘c’ is in both words, and is pronounced differently in each. ‘c’ can sound like either ‘k’ or ‘s’. That’s how it works w…