As someone whos been doing coast runs since before kiters invented downwinders (since the 90s) I would mention we always try and have a "buddy" system a bit like scuba divers. Keep an eye on where the others are so when someone breaks something you know where to look for them. If its a big group pairing off so you are each responsible for one other would make it simpler.
I have had a few over the years where you loose track and think someones lost only to have them turn up at the end. It takes some of the fun out of the rest of the sail thinking about what you are going to tell his wife when you ring her and then call the search and rescue to try and find him.
We have also had a few injuries where you have to help the injured sailor to shore or at least keep and eye on him so you know he got there ok. A broken foot was the worst I can recall any of us getting. Equipment breakages are probably more likely and again knowing someone knows you are out there makes the swim in a bit less taxing.
Have fun and keep safe.
PS: FYI tracks of my recent runs at
funstuff.nanotera.com.auPPS: Any photos of your sister ? just to keep troppo happy (Im enjoying the 5.8 you sold me but it was too big yesterday)