New cars are not nearly as inflated. The answer to the first question is yes, it's a very good time to sell old and buy new. One stipulation is that ordering a new vehicle with specifications they don't have on the lot will take in the realm of 6 months. Pretty big trade off, but I'm about to deal with this myself and can afford the time difference.
New cars aren't nearly as inflated, but the higher starting price of a new car means the absolute change is still more than a use car.
Talk to some dealerships, some are buying 1 year used cars and giving new cars at discounts
you certainly won't be finding a deal new. friend of mine's father owns a group of dealerships in the town, they have people going to other dealers paying MSRP just to have inventory on their lots and sell for more obviously
Yes you can. You just have to shop around. I got well below MSRP out the door a few months ago.