Its a good question and their advice is not helpful (though correct), however watering is something you really have to learn by observing, which you are!
In hot weather, and even more when windy with dry air as at the moment, plants transpire a lot of water. Even more when they are growing strongly, as with tomatoes at present. And large plants transpire more water than small ones.
So you will find a greater need to water as the season progresses, except on dull, damp days, but even then keep an eye on the soil dryness because of the plants’ size.
Water a little less in September to encourage ripening of fruit, rather than general growth.