I'd ask the pros here, but I wonder if you won't have some major problems when your plants get bigger having so many in a small pot. I wonder if you couldn't cut a couple out down to a single plant and take the cut ones and replant them. Usually doesn't take long for them to develop new roots, since your plants are in a small stage right now. That's what I'd do, but ask a few other folks about doing it.
I prune the bottom leaves of my containers. Water splashes up even with them and things float on the air you don't see to land on your soil. I do the bottom leaves go up a bit and as the plant gets taller then I cut off more and more bottom leaves til I have a foot or better of just stem showing.
I agree with Ed. Those meters are usually pretty accurate. Haven't had one go wrong myself either. You might want to water. Wait and hour or two and then check your soil. That will give the soil plenty of time to absorb moisture and if it still dry when you re-check then add some more water and re-check again after a few hours.
One thing to remember too is that while the tops of your pot may dry out fast, the bottoms can be very wet. You don't want to over water or you'll rot your roots. Not sure if you can check or not, but I check bottom holes too to feel if bottom of pot is wet.
Takes a little practice to get the hang of container watering and it changes as the weather does. Me, I have learned to count seconds for each pot for watering. It works for me and I finally had learned to quit drowning or starving the plants. You'll find your rhythm.
The answer to all your problems are on this site and with the pros. Don't be afraid to ask. Little questions, big questions, they have the answers. Looking forward to when you post your first tomato pic. : )
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