I use a small percentage of my Pro token quota to find better deals on hotels, rental cars, discount codes for large purchases, etc. Have it automatically scanning credit card points promos and flight deals via various APIs too. Easily pays for itself in that regard. Over $1k, I'm not sure it would break even anymore.
For flights, SerpApi (to get Google Flights data) in combination with seats.aero pro. I use data from those services with a MILP library where I provide various travel and cost constraints. Runs periodically and notifies me of any good deals. I don't know if my setup actually does much more than the more expensive paid services already out there, but I can at least customize it a lot more to my liking to avoid a lot of manual search effort.
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