Here's my take on the Skyway--it is an advanced kiting spot and should be avoided by all beginners and many intermediate riders if they are not riding there with an instructor. Why? Here's a few reasons:

The launch is tight. The entire time you are kiting, you are upwind of an interstate highway. There is sharp stuff out there that can gash you. There are rocks out there. The wind is unstable in certain spots, particularly at the launch. The water is deep to both the left and right of the main riding area and if you put your kite down in there and can not relaunch, you are probably going to get dragged to a rocky shore close to the highway. It is necessary to stay upwind when riding at the Skyway to stay out of trouble, no matter the wind direction. It interferes with the ability of even advanced riders at the Skyway to ride safely when a beginner is foundering 20 feet upwind of the beach with the kite at 12:00 o'clock. There are spectators who pull off I-275 to watch what is going on. It is crowded. There are many new riders who ride there who are a hazard to other riders on the water. If you lose your kite, it is probably going to be destroyed.

Perhaps some will counter by saying that on a NE, E, or SE wind, the Skyway is the closest place to them to ride. I think that is irrelevant to whether a rider should even be on the water there. That's like a new surfer saying that the closest break to him is Pipeline. The spot is still too heavy. When I was still learning to be independent as a rider, I avoided the Skyway for almost an entire year (after a kitemare there that almost involved going under the bridge) before deciding I was up to it. Part of being a kiteboarder is learning to identify your own limitations and then not push too far beyond them to avoid hurting yourself or someone else.

As far as helping others out, I see that going on all the time. I have given help and received help. Notwithstanding that, there is no duty on me to serve as a lifeguard and spend my session watching over other riders. Part of being a kiteboarder is knowing that when you go out, you will make certain that you come back in under your own power, not with the crew or the Coast Guard or a bystanding jet-skier or someone else performing a rescue. If you have doubt, don't go out. If you want someone to have your back, make a deal with a friend with more riding skill or hire an instructor for the session.

If you are unmoved by these warnings and must go out at the Skyway without a full bag of skillz, do this: launch, get in the water without delay, then (keeping the kite about 25 feet off of the water at the edge of the window), walk all the way out to the sandbar and start riding there. That way, you will have some downwind room to give and might actually be able to progress at the Skyway. It will take you 5 to 10 minutes to walk out there, so rig smaller, bring a bigger board, and maybe you won't get worked.