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Plain Applescript can't do always-on-top windows. Perhaps Applescript Studio or an extension would help.

I think a neat OF feature might be a "What's Next" window. It would show a single next action. The next action could be the very first one in the current context view. (Or it could be based on a perspective, or on the view bar settings when the What's Next window was opened.)

The What's Next window would be (optionally) always on top. Check off the task in the window would cause the next task to be displayed.