I am not 法居士, but I can help
I had exact some situation as you are having. My OPT was expired this August and my H-1 started in Oct. I also had two months gap period. For your case,
1. Your H-1 will start on 10/1/2006. You do have a two months gap. You can not work during that period of time. If possible, you can ask your company if you can be "on-leave" for that period of time (without pay most likely).
2. The two months gap should not be a problem for your legal status because we can have a 90 days grace period. You do not need to leave the country for that two months.
Hopefully my messages helps.