STORY OF SEASONS: Pioneers of Olive Town

This is a cumulative trophy that will collect progress over time from you watering your crops. Your watering can will hardly hold much early on, but will graduate into holding at least 99 instances of water once fully upgraded. You can check your progress on this in two ways:

1) On the Title Screen, there is a trophy icon that allows you to check in on your trophy progress for all unlockable trophies with Playstation. It will show you the progress of this and many more, such as when it asks you to craft 2,000 items.
2) In-game, go to the far left page in your menu screen for Records. Opt to access the Change Titles screen and then go to the corresponding field for the trophy you're interested in. For the sake of this trophy, Harvesting/Fieldwork will be the field that allows you to track progress.

Try not to worry too much about the progress of this trophy, as it will unlock naturally through progress anyway. If it doesn't unlock by the end of summer, increase the amount of plants you're growing through the season; you'll notice a fair increase in stamina consumption, but also in the amount of money you'd be making.