Answer: Much of gardening is an experiment and we learn as we go along, so give it a try and see what happens. The containers sound fine, as do the soil and location. Watering will depend on the weather, whether or not it has rained or been windy, how large the plants grow, how hot it is and what type of soil mix you use.
Fertilizer will leach out eventually, but you will see your plants begin to slow and thus know it is time to supplement the mix. Tomatoes are heavy feeders but it is better to underfertilize than overfertilize so don't worry about it too much, just keep an eye on the plants and they will tell you. You can always topdress with compost if in doubt.
You might try one tomato in each tub (perhaps one a cherry and one a larger fruited tomato) because these are rather large plants. Alongside them you might try several basils or one pepper, since peppers can also become good sized plants. You might also tuck in a few bush beans early on, as they will produce and then fade and be removed to make more room for the tomatoes. You could also add some more smaller herbs such as parsley, chives, or thyme around the outer edges, or even a dwarf marigold or two.
Enjoy your containers!
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