We've almost always done splits in order to try out new resorts, too, and I agree with PP that moving 2x the most we like to do, but if 3x is what you get, it's not the end of the world by any stretch.
We are COO, and each of us has color-coded packing cubes per person. I prefer the small, narrow packing cubes, and put one outfit per day in there, per person, with a bathing suit. For the girls, we prefer sundresses with bike shorts underneath (or your bathing suit under the dress for moving day.)
For the boys, tank tops and (bathing) shorts. We all do sandals or crocs with ankle straps for support and in case of downpours. No flip-flops to slide around in at MK! Keep an extra pair of dry socks safe in ziploc bags in your day backpack. We also use Camelback backpacks for everyone and fill the bladder up every day with fresh ice water. Saves money and hands in the parks, and even the kids can sip all day in the heat from the straw.
Our kids only care about the pools and arts and crafts. I'd maximize each check-out day to have a great brunch reservation somewhere and then head to the next resort and hit their pool on a full belly. Let the kids shake it out while one parent hits the front desk know you're there. Bell services will move your luggage from resort to resort, but groceries you're responsible for.
While you're waiting at the pool, throw a load of laundry in while killing time. Have a drink/snack/coffee midday and check out the community room/activities calendar and all dining offered.
We really enjoy the resorts as much as the parks, and with all the moving you'll be doing, I'd view daytime as exploring resorts/pools/restaurants time, and we hit the parks after 5 p.m. most days. When the strollers move out, we move in!
We bring the kids' stuffies and favorite throw blanket in their backpacks, even years later at age 10 and 11. This is the first thing they unpack for their beds at each resort, and it gets chilly in the rooms with AC! This way they can crash when you're let into the new room and maybe take a little power nap or just get their bearings in a new place while you guys unpack/get settled.
Also, slipper socks for everyone. Again, it gets cold, and we don't like dirty feet in the bed. I also pack sleep masks for everyone. That Florida sun is tough to block out for napping, especially in a new environment. You want the kids to feel relaxed, if possible, so they actually can sleep. We also have sound machines for each room. They're like $20 on
Amazon and the size of a square hockey puck.
If you're doing studios, mac and cheese cups and/or oatmeal cups are great in a pinch for microwaving as a snack at night and don't require refrigeration. We always get groceries delivered, and I'd do bottled water and shelf-stable milk.
Don't overpack clothes. We now only bring three outfits every trip. I do laundry every day, and it's honestly no big deal (to me.) We DO bring/bought bathrobes for everyone. We love the hot tubs at night, and I feel funny walking through the resorts in a bathing suit and towel. Sometimes it's cold, too, and you want that layer of warmth. We use the compression bags for those in the suitcase.
Investigate Owners Lockers. They don't save us money, but they are a life-saver for all the toiletries and sunblock and chargers and seasonal-specific stuff we use at the parks. We leave our Camelbacks in there, too, because we don't use them anywhere else but the parks. I don't bother with the kids' stuff because every trip is a different season/size as they grow, but my husband and I have a decent wardrobe of staples in there; socks, underwear, bathing suit, strapless bra for sundresses, water park shoes, etc.
