Tough to pull off with that many elements on top of each other. Usually you can tell you might have a legibility issue when you lean too heavily on an outline to pull it off.
Awful lot of noise in the logo; specifically the blue Gulfside, with white outline, then black outline. Visually, that causes a lot of vibrations, and makes it hard to stand out.
Try and break it down to focal points, and order your copy in terms of importance, via primary and seconary. Right now, its a little hard to pull off because your two main elements compete, and somewhat clash.
Usually you know you have a slight problem with a design when it can't be embroidered because of all the details.