Hmmm maybe it's just that I am usually not tied to a date, e.g. having to fly on a Saturday, or having to do this in August? But sometimes I am and even then I don't tend to pay anywhere near as much?
I do tend to put time into planning and book on price though. To an extent I also choose destination on price, e.g. if I want to go to Switzerland, I'll go in May or September as opposed to July if it's better value. I do tend to stay away from crowded places, e.g. avoid Spain and Italy in August. If I was tied to school holidy dates, I'd probably choose a less popular destination like Montenegro.
E.g. always use Skyscanner for flights, if Wednesday flight is 100 and Friday is 300, I will fly on Wednesday. Their calendar feature I find very helpful, showing which days are higher and which ones lower prices.
Hotels is the same, I tend to choose 1-2 hotels I want, open the 'shop by price' calendar and find the week that's best priced. Usually that also means quieter, which makes for a better stay for me. I'm also happy to Airbnb for more space/ if a bigger group is travelling.
I don't really do budget airlines if I can help it and out-of-way airports or 6am flights as they stress me out 😂So tend to choose an afternoon or evening flight and generally prefer a relaxed transfer approach.
Usually book fairly close to travel time, maybe 3 weeks. Booked a flight yesterday and BA price had dropped below Ryanair's now that we are closer to travel dates, so booked that instead.
With hotels, sometimes I book a loooong time in advance with flexible cancellation. The closer to time, 1-6 weeks out and once flights are booked, I monitor prices and see if a better hotel is available at an improved price.
Have never used an agent or booked a package holiday or an all inclusive. That's what I assumed created the high prices quoted here. But equally it does remove the time spent on self-planning.
My mum paid 3K for a package holiday recently and I was shocked as I knew I could have booked her the same holiday but with much better hotels and more tailored to her needs & wants for half the price.
Sorry for the long post, hope it's somewhat helpful, if nothing revolutionary.