I know this is such a minor thing, but I wonder if the crew had the Season 3 and beyond uniforms in Seasons 1 and 2, if those seasons would have been better. There are some classic episodes in both those seasons, worthy to be called some of the best that TNG had to offer.
I really think that is somewhat part of it, or at least for me. I was 17 when TNG premiered and watched half of the premiere and turned it off (captain is too old, no vulcans, WTF is up with the skirts on dudes). Later in college, I started watching season 3 and fell in love. I watched all of S1 and S2 on reruns and found the outfits and production a little jarring.
I've recently rewatched the entire series and was pleasantly surprised how the first 2 seasons really weren't as bad as I remembered.