My wife and I love to travel ... a lot! However ... we tend to have ONE recurring problem: we always find ourselves in icky situations when making bookings because we continually have clashes with flights and hotels. This leads to us getting trapped in a location for longer than desired, purely because we have to "wait it out", either with a hotel we have booked, or a flight that cannot be changed.
It's super frustrating. If we don't book in advance then we risk missing out on a hotel, or a flight, and usually pay a far greater price for leaving it so late.
One way around this, which we have started taking seriously, is to fork out the extra dough upfront for a cancellable airfare. Usually to cancel or change a flight it costs you a few hundred bucks. Most times, especially here in the US, airlines make you jump through hoops to have even the slightest chance of making a change.
That's why they offer a tiered pricing model where you can upgrade to have that flexibility. Usually it's not needed, but for us, it's something we seriously need to consider. Yeah, it stings when paying for stuff you might not need - like insurance... But the alternative is generally even more sucky.