I don’t like it because I don’t need it. I only like it on my travel watch, but I don’t think I’ve really needed to know the date in years. And if I did, I’d be on a computer which has the date right there at a glance.
It also makes it more of a hassle to set the watch if it winds down. Not a huge hassle, but still.
Third, it usually just doesn’t look good or isn’t well executed. To me, watches are mostly jewelry so looks / design are some of the most important aspects, and very few date windows actually enhance the design aspect of a watch. Some are ok, and most just look lazily tacked on after the design was finished.
So in short: mostly looks bad, makes watches more annoying, and I never use or need it. So that’s two negatives vs zero positives, for me personally at least.
For me it’s a bit of both - I don’t feel like I need to be checking boxes, but every watch needs to be worn somewhat regularly. I have other hobbies and having thousands just sit in a watchbox isn’t something I want to afford.
I don’t need a chronograph and I don’t need a diver, because I either don’t particularly like the style or don’t think they’re worth the hassle, but I need a dress watch because I actually like wearing them and they make more sense for my lifestyle.