This is an excellent question!
I have a huge list of places I want to see, and tend not to want to repeat destinations (exception: if Boyfriend hasn’t been there and really really wants to go).
I usually start with some rough parameters when narrowing it down - like, when I settled on Cape Cod it was someplace I haven’t been/that is pretty and has scenery and water/relatively inexpensive flight/Boyfriend doesn’t care about going there as this was a solo trip/good weather in July.
When we went to Los Angeles, it was someplace that’s warm in early April/and has a beach/that we haven’t been to/that has Things to Do/and is not a usual beach tourist destination like Florida/and isn’t too expensive to fly to.
Being able to fly directly with no layovers is also pretty important to me, as I’ve lost entire days off trips due to sitting in some airport. So if it’s super expensive to get there without taking a bunch of short hops (looking at you Southwest!) then I’d really need convincing to choose that destination.
If I’m planning a big bucket list trip then I just shovel savings into my “vacation fund” like a madwoman, sometimes to the exclusion of other goals. This is how we did Maui in February 2020. If it’s a smaller trip, like a long weekend, then I generally just try and keep flight/hotel inexpensive but not terrible.
As I get older I seem to be prioritizing scenery that’s different from the Midwest, over experiences. Beach, mountains, desert, tropics.
Re Hawaii… I found the flight to be punishingly long and very unpleasant even though it was nonstop - and I am not six. And you’re farther east than I am.