I did not load every email into the context window at once, and I did not use a literal sliding window over your entire inbox.
I treated Gmail more like a database that I could query repeatedly. The overall pattern was:
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Search narrowly for candidate travel emails. I queried Gmail by year and by travel-oriented terms/providers: Airbnb, Alaska, Delta, Southwest, Booking.com, Vrbo, Turo, Expedia, “check in,” “trip,” “reservation,” etc. That gives a relatively small candidate set rather than thousands of unrelated emails.
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Read only the promising messages. Search results usually give enough metadata/snippets to decide which emails matter. I then opened specific messages—receipts, boarding/check-in emails, hotel folios, post-stay reviews, rental confirmations—and extracted the useful facts:
- dates
- origin/destination