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I'm afraid there is no way to track time on a checklist item, The only option to track time would be on a card level.
For instance: Harvest does have a Trello Power-up, so you can enable this on your board. Once you have authorised the Power-up, you should then be able to enter your time from the back of each card. You can see more about the features here: https://blog.getharvest.com/2016/01/new-the-harvest-power-up-for-trello/
Here are a few other time tracking powerups: https://trello.com/power-ups/search?q=time%20tracking
Vishaal S | The Trello Team