I'm discovering that the prerelease version of Bob Harper's
Practical Foundations for Programming Languages has answers to many of the questions that have been bugging me.
It's 51 chapters, but many of the chapters are short and reasonably independent of one another, so that you can get yourself up to speed on a particular topic without investing the time to read the entire thing.
The book is at
http://www.cs.cmu.edu/~rwh/plbook/book.pdf .
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