Although it looks and is cool you need more then beginner skills to ride directionals. I think your money would be better spent on a used or closeout (sales on now) big light wind Twintip
If you have wakeboard experience, a twintip may be easier.
If you have a little snowboard experience, it does not necessarily transfer well.
If you have surfing experience, or windsurfing, a directional will feel "natural" from day one, and
you can actually go upwind on your first day, on a directional. You won't make jibes on any board for a while, so don't worry about that.
I would say stop buying stuff, too..
The key is to speed your learning by concentrating on one thing at a time.
So, if there is any kind of board you're good at riding start with that kind!
Otherwise you may flail around trying to learn too many things at once for many sessions, all the while hearing instructors try to encourage you and talk about the "learning curve," they may say is "huge" or "vertical." Another, honest way to describe that is to say it's like a brick wall. It takes a lot to climb over it. Breaking it into steps is a more useful concept.
If you have no boardsports experience and are committed to trying a twintip, take the trouble to learn to ride your kiteboard behind a boat or ski for a few hours, so you can switch directions and have some idea of edge control, before trying to learn all that, plus how to fly the kite at once.
It can also help if you have some sailing background, but it isn't really all that necessary.
Take a lesson, enjoy it.
Try 2-3 types of kite to see what you like.
The cabrinha is a fairly good bet for starting though, good range and depower.
The shops are thin on the ground in SW Fl.
The outfit in Ft Myers is odd. My impression is it's basically a windsurf/SUP store, that usually employs a young guy to teach kiters. I think they sell cabrinha.
If you do buy a directional, I would second the Slingshot dialer, it is big and very stable, and goes upwind well, good in light wind. Also the nugget, but try some things before making the commitment. And like Munney said, don't go for the long, sharp fins first.