Pushing the zone in a new zone

We bought our farm 2 years ago, moving from Maryland(zone 7b) to North Central Florida(zone 8b/9a). Of course, one of the first things I did was build a garden - slightly raised beds built with trench composting of food, sticks, yard debris, rotting logs, manure and anything else I could get my hands on. I planted tons of perennials that are doing great - elder, blackberry, blueberry, ginger, turmeric, sweet potatoes, herbs, etc.

Annual stuff, however, is giving me fits. Back in Maryland, I could grow beautiful tomatoes, squash, beans, potatoes, spinach...you get the idea. I was able to put up enough veggies and sauces to get us through winter.

Florida, though...last year, I concentrated on the structural/perennial plants. They did so well that I decided to move on to annuals. I followed the zone-specific planting guide from Mary's Heirloom Seeds. FAIL. I got a handful of beans, a couple tomatoes, a few carrots. The squash bugs feasted on yellow squash, zucchini, pumpkin and various winter squash varieties. I fought off the army worms so I could keep some of the greens. I got a few, but not nearly as much as I planned. Potatoes did okay, but I had to pull them early because of the bugs.

WE HAVE NO WORMS. Even with the new, better moisture retention, worms are non-existent in our area unless you build a worm box and order them in.

The "cool weather" crops like kale, collards, cabbage and asparagus are flourishing. In July, when a good temperature description is "sauna stoked by hellfire." So are the Roselle and sunflowers, which are heat lovers. My Everglades tomatoes are fruiting to beat the band, but they're tiny so I'm not going to can them.

My garden seems to be bipolar.

So I've decided to throw everything at the garden and hope something sticks. This morning, I put in seeds for pumpkin, winter squash, peanuts, tomatoes, peppers, cucumbers, bush and pole beans. Tomorrow I'll throw in some more cabbage, kale and collards, along with beets, turnips, carrots and whatever else I find in my stash of old seeds.

I called this post pushing the zone because the only things I'm supposed to plant are tomatoes, peppers, cucumber, pumpkin and Southern peas.

Any thoughts or recommendations?

I've read a lot of his stuff. This year has been weird even according to the oldtimers. Hence my deciding to push the zone and look for ideas/recommendations on that concept. I guess what I'm really looking for is ideas on further pushing it.

How about okra, watermelons, and sweet potatoes? I've never lived in Florida, but I've heard they're some of the few common annual vegetables that thrive in Florida summers and sandy soil. Here in Missouri they certainly thrive in summers we sometimes get that get hot enough to stress tomatoes and halt green bean production in its tracks.

Also, have you ever eaten the sweet potato greens? They make a real good cooked green, I start harvesting greens from my plants when they're big enough that taking a small percentage of their greens won't really interfere with productivity of the roots. It's just the time that few other greens are coming in due to the heat.

I'm starting my second round of tomatoes - they're typically done by June, and you can start a second batch in July or August. Watermelon is going in sometime this week - first harvest finished a couple weeks ago. (Not MY harvest, because mine got eaten by bugs!)

It's just so weird to me that the winter vegetables are doing better than the summer ones.