Been thinking about this question a lot recently, as my opinions on a watch often changes after a few days, a week, and then a few months after wearing a watch.
What's worse is that an initial impression after just a few minutes of trying something on at the AD is not enough to make an informed decision. I really wish there was some way of trying a watch for a while before having to purchase it. Even if i was able to wear it for an afternoon or a day, that would be extremely helpful.
For example, a car dealer once let me take a car home for the night, telling me "taking it for the night, drive it around, take your time! I want you to buy it, but I also want you to be happy with the choice." I ended up buying the car. Not sure if AD's ever do that?
I'm guessing a lot of people (like myself) sometimes buys something just to try it out, but then you take a hit in trying to flip it if it doesn't work out. As I've been trying to go after "higher-end" pieces, instead of buying multiple "mid-tier" watches, this is becoming more of an issue.
On the other hand, maybe this is all part of the fun - constantly looking, researching, and thinking about your next purchase.
Would love to hear what others think!