That's an interesting one, and I've been annoyed by my own tagging of the year.
Ultimately, preference rules, but I know I use the year as a selectable column on my Media Center Home Page (if you will) so I can easily see albums from (usually) the current year. For me the most important reason for tagging is providing a variety of ways of build lists of things to play. With that in mind, I am always changing the year to reflect the song or albums original release date, even if it is part of a new release. I realize this would not be the purist option. So example, I would not want the Woodstock 69 re-releases under the year 2020, but rather under the original release date. Some might give me twenty lashes for this. The three pre-defined date tag fields (Year, Year Album, and Date) are the same across all three fields (aside from some formatting) in my drive, without me making this so. I tend to: 1)Not keep a duplicate track from both an original release and a re-mastered. I sometimes make an exception if they are way different and both worthy, and 2) Put the "remastered" label as part of the album name, if that is what it is. But mostly I'm lazy and my files are a mess!
Larry