Hi Bristol, I hope you don't mind me offering my comments to your thread.
I went in September/October about 4 or 5 years ago. It was gusty. Gusty. Gusty.
Having said that, the gusty wind was okay the further you got out, and in the speed strip it was okay. I preferred to use the larger V8 (i.e. cammed) sails as they were much better in the gusts than the wave sails that were used for almost everything else.
I stayed the first week and a half at the Coralia, and sailed with the Harry Nass hire centre, and the next week and a half I stayed at the Hilton and sailed at Club Mistral/Club Dahab. I felt that Club Mistral had a better range of gear to suit me and my weight, as they had more cammed sails in the smaller sizes.
One thing to watch is that most of these resorts have you reserve a board for your exclusive use. If you don't use it, no one else gets to use it either. You can use any other unreserved boards, but there aren't that many.
My mistake was that I reserved a 115L board which for my weight at the time was almost a sinker. The problem is that it is so gusty that it was too small, and all of the 130L boards were reserved. I had to find whatever I could and often used a 140L or bigger boards.
Next time I would reserve a bigger board.
Other thing I would recommend is bludging a lift from the rescue boats to take you back out to the speed strip. Much faster and easier

I also took a camel back, which was a great idea as it takes ages to get back to shore, so you don't really want to go in for a drink.
The taxi ride from SSH is much better if you prearrange it with your hotel. The normal taxis are not airconditioned and a bit of a monopoly, so in my case you can get charged a lot, and I think I paid something like $100 USD. The hotel organised return trip was something like $25 USD.
I wish I was there for longer as it was a worry avoiding the local restaurants for fear of catching the bacteria that give you 'Dahab Dash'. The prices of food were good and it smelled excellent, so it was sad to stick to boring/bland hotel food. Not that the food in the hotels were bad, but the local stuff seemed better.
If I make it back there next time, I will avoid Cairo altogether and fly to SSH either on a Euro tour plane, or change the same day in Cairo.