Welcome to FT, FlyingactressT.
I find the best way to minimize luggage troubles is to only bring a carry-on. I use a lightweight spinner, so that it can even be rolled down the airplane aisle. On top of it, I use a travel tote of medium/large size. It's not so big that it flops around on the roller handle, but big enough to carry a change of clothes, my spare sandals, the laptop, etc.
You are going to a warm destination, so, with a little effort, you should be able to pack lightly. Then the double connection won't matter a lick- everything you brought will be with you.
See this thread for fun stories and suggestions:
http://www.flyertalk.com/forum/trave...ust-carry.html