I'm not sure if this helps, but there are quite a few local and semi-local cycling coaches around. Most of the coaching is geared towards fitness and racing.
I've heard that Bob McCarty does some skills building classes too. He is out of south Florida, but follows the FSC races and will often have classes in the days before a race at the various locations. It can't hurt to inquire I guess. http://www.mccartytraining.com/
Also, Drew Edsall is another racer/coach that offers fitness oriented coaching. I'm not sure if he provides any skill building, but he is a nice guy. He isn't local and spends part of they year out of state, but I vaguely recall him coming back to FL for the winters. http://www.coachdrewedsall.com/
Unfortunately, most of the coaching for cycling is centered around fitness, so it's hard to find a skills building coach. The landscape of FL makes it even less likely, because we don't have the same big technical features that others states do. In my opinion, the best solution is to get out and ride more. Try to find guys with similar fitness that might have better handling skills and watch how they approach obstacles. Most of the technical stuff in Florida can be conquered with a little confidence and more speed on the approach. Good luck.