The cumulative trophy for Grim Fandango: Remastered, this trophy requires you, more than anything, to exhaust every conversational topic with several possible people in each year. Each of the four years have additional information associated with them, so I would suggest looking into them for the specific trophies for each year.
Furthermore, there is one trophy that would require you to make sure that you start the game, and then immediately start another.
Most of the trophies in this game are optional, with only a handful that are actually given as a part of the story. These are:
In Year Two:
In Year Four:
There are fourteen trophies found within Year One, a fifteenth given for completing the first year itself.
There are fifteen trophies found within Year Two, a sixteenth given for completing the second year.
There are six trophies associated with the time spent in Year Three, a seventh given when you complete the third year.
There are seven trophies given during Year Four, an eighth when you complete the game.
With the last two being the tank control trophy and the platinum, that equals about right. As I mentioned, refer to the corresponding year trophies for information or links on how to get the optional trophies in their respective years. Thank you, DoubleFine, for bringing us this lovely masterpiece to the newer generation without losing its charm.