By considering places I went to, what I liked and what I didn't like about them, what I would like to experience and what I wouldn't like to experienced based on past experiences, popularity, trouble-free area, costs, PITA factor when it comes to mobility, etc... I'm an indecisive traveler and I like to explore.
I look at insurance costs, versatility of the car, potential value retention, reliability, demand for resale, etc... Not all the boxes always get checked. I do like my cars to have higher trims and more power—they just resell better and are more enjoyable.
How do you know immediately whether you'll like where you've arrived to vacation?