1. Lead times aren't too long on the 997 now. Phone around a few OPC's and you should be able to get one to your spec within 3/4 months.
2. I've not heard of dealers not accepting orders if you don't add loads of options. In fact my new Boxster has only Pounds3k of options. If a dealer says that to you, then just walk away, there will be another dealer willing to take your order.
3. Can't help with the insurance, as my car is on a fleet policy