Earlier quoted context omitted.
> I have to constantly min-max the costs between hotels on certain days, flights on certain days, and cars on certain days. I agree it's a burdensome chore! Just wondering - your hotel stay can't be less than the days between your flight. For car, one can manage to cut down with Uber/public transport, but still turns out to be expensive than a rental car.
> your hotel stay can't be less than the days between your flight. This is exactly right, and why it's such a pain. Because if I have a bit of flexibility, I have to figure out which flying day is best for prices and seats, and then see if the hotel is more or less between those days. For example, if I fly on Tuesday I can save $400 vs flying Sunday. But if I want to stay a week, the hotel may not have the following…
Recently, I've been travelling for events, so my dates are fixed, and that's why I could not connect with your scenario! Travel bookings and other web searches are ripe for automation. Even if the system can bring down the search results to the final 3 instead of a complete automation, I'd still call it a win. Shameless plug, I'm working on such an agent, although currently at a very early stage.
> I only trust myself, my wife, and my sister in law to get this right.
Can you please elaborate on that? Do others not look at cost savings across the board and focus only on one item out of all?