I don't have all of those answers but I can hopefully help you out a little bit.
The final day of production for the 2014 Corvette is August 8 and the first day of production for the 2015 Corvette is August 11. So the
earliest that you could expect a vehicle would probably be 5 or 6 weeks after that date. But that will only happen if you are at the front of the line at a large dealership AND get a little lucky. If there is a large demand at first just like with the 2014 Corvette, your wait could be a few weeks or months longer, but Les Stanford is one of the biggest Corvette Dealerships so if you order from them and I would imagine that you would have it by the end of October at the absolute latest (as long as you are at the top of the list and the dealer has an allocation for your order). Most of the horror stories come from people who order from smaller dealerships and have an item or items on constraint. I would highly suggest only ordering from one of the top 8 largest Corvette dealrships in the country. They are the ones with the majority of the allocations and they WILL get your car built without any horror stories. You can start placing orders for the 2015 Corvette on June 26, 2014.
There will definitely be a price increase in 2015 but I do not have any inside information on how much it will be. They cannot keep up with the demand for the Z51 package so there will likely be another significant increase on that as well.
The options that you choose have to be up to you. But I would recommend AT LEAST getting the Performance Exhaust. I would also recommend the Z51 Package, Magnetic Selective Ride Control, and the Carbon Fiber Interior Trim if you can afford it and if they are no longer on constraint by then.
Good luck! And let us know if you have any other questions