Well, you typically lose the most value in the first year of ownership. With that said, you might find a good deal in the coming months (especially as the year draws to a close) as dealerships look to move current inventory to make room for the 2015s.
Depends on the dealer. I have gotten great deals on my trade ins and new cars at the dealer I was using. Of course knowing everybody there because I worked at that dealer helps.
You'll probably take a bath! It can't hurt to chat with them. You'll probably get between 25-29k for the trade..possibly a tad more since you only have 9k miles. Best scenario would be them agreeing to keep your payment at what it is now and tack on the additional balance. You'll be upside down which sucks, but you'd have your SRT.
Look for leftovers too, they can be had for mid to low 40s. This way the pain won't be as bad.
1. Come up with numbers acceptable to you. (Check NADA, KBB.COM and other car price/trade-in guides)
2. Go to dealer, have the attitude that you don't care if you get the car or not (important).
3. Start low, real low and move up slowly.
4. Don't go higher than #1
5. Don't be afraid to walk. They'll call you back in a few days.