You have several things going on: cracking indicates dry soil...then watering causes the fruit to crack. Keep the plants as evenly moist as possible...potting soil dries out very quickly...top dress a bit away from the trunk with composted manure (Black Cow, for example), then cover that with mulch to keep splashback from the manure off the plants (especially fruit).
The wrinkled dry mottled leaves may be tobacco mosaic virus, but the plants will still produce if you take care of them. The virus is plant only, and will not harm people.
Pests tend to attack plants that are stressed, like yours. I can't see the pests. but insects carry a number of diseases: fungal, bacterial, and viral. If the plant leaves stay dry, they may have spider mites (which have tiny webs at the nodes of leaf petiole and branch). Chili thrips may be the insect in question, can't tell.
Due to the round nature of the sunken holes and mushy contents, it is probably a bacterial disease, a result of insect damage.
Throw the tomato fruits away, but do not compost them. You can use a level teaspoon of non-grease-cutting dish soap (the cheap stuff), and a level teaspoon of baking soda in a gallon of lukewarm water, mix well and spray on the plants in the evening, when it is cooler (relatively). If it gets washed off, reapply. This concoction may burn the plants if applied in the hot sun (as would plain water) leaving water spots, another way for diseases to enter the plant. If you compost, dress the plants with this, and make sure they get enough water...early morning is best. Florida summers are hard on tomatoes...afternoon shade may be helpful.
Good luck.

Thank you for the reply :) We are using Neem oil right now and it seems to be controlling the pests...only a couple of plants are affected so hopefully it won't spread.
I was reading that stink bugs will take a "bite" out of the fruit thus allowing bacterial or fungal disease to take hold...we have seen a couple of those bugs o occasion.
Never heard of using baking soda in the spray..willing to give that a try but not sure if it will have a reaction with the Neem. Keeping fingers crossed here but we have had a pretty good yield from the healthy plants.
No shade here to speak of so we do the best we can as far as watering.
Again thanks for your help!

I just discovered a pest on my tomatos that going to town on them. Can't tell if they are spiders or mites, very small, and rust in color. I've tried soapy water, Sevin, and Ortho Max. So far none of these three is stopping them. Anyone have an idea what these are or what to use? I've looked all over and can't find anything that looks like these.