Why you should know: The ‘a’ vs ‘an’ conundrum is not about what letter actually begins the word, but instead about how the sound of the word starts.
For example, the ‘h’ in ‘hour’ is silent, so you would say ‘an hour’ and not ‘a hour’. A trickier example is Ukraine: because the ‘U’ is pronounced as ‘You’, and in this case the ‘y’ is a consonant, you would say “a Ukraine” and not “an Ukraine”.
Tip: when in doubt, sound it out(loud).
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English is definitely nuts, but can you give an example of where this particular rule doesn’t apply?
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All of the examples relate to differences in pronunciation, so the guidance in the OP is good - use your personal pronunciation. I would imagine this would be harder for non-native speakers, but fortunately there aren’t many words (that I’m aware of) that are commonly pronounced with a leading vowel sound or leading consonant sound depending of dialect.
The only example cited in this thread that most people will experience is “herb” which has large populations that pronounce it with and without a silent “h.” “History” and related words are not commonly pronounced with a silent h outside of regional dialects.