Hi Mallory! First of all, let me just say that I am constantly blown away by your cookies. You've got such unique style and incredible talent.
Secondly, with regard to moving to a state with a Cottage Food Law: Research the state laws VERY carefully. I live in a state with a Cottage Food Law that prohibits shipping, selling online and selling to a third party (i.e. a store or bakery that would then sell your cookies to their customers). So if I had gone to all the trouble of modifying my kitchen and getting inspected and certified, I'd only be allowed to sell directly to customers, pretty much limiting me to farmers' markets. I decided it didn't make any financial sense to jump through all the hoops to get my home kitchen licensed and then have such limitations imposed on my business. The best option for me was to rent time in a commercial kitchen. I live in a major metropolitan area so it sounds like that's much easier for me than for you in Florida.
There are states with cottage laws that are much more lax than mine, so if you're seriously looking at moving to a location BECAUSE of the cottage law, make sure you choose a state with the least limitations.
I hope this helps!
Tracey