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Is it possible to can't find a balance in between? It doesn't HAVE to be an all-or-nothing decision.
If 300 monsters is unwieldy, then what about breaking it down into a 3-6 files? You could have 3 files of 100 monsters apiece, separating them alphabetically like is done for the stock portfolios. Or you could have 6 files of 50 monsters apiece. Or somewhere in between.
This way, you end up with a low number of files that aren't likely to get confused by anyone, while still keeping them highly maintainable.
Just an idea to consider....
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