I think your right and I will go with the 16. Now, do I need to wait till December 9th for my Verizon contract to expire, or can I do it this couple of weeks early?
Here's what I recommend: Get the iPhone now (or, wait till Black Friday to see if deals pop up on it), but
do not port your number over. let AT&T give you one of their numbers.
Then, use the time between now and December 9 to test out the phone and make sure you're happy with it.
If you are NOT happy, then just return the iPhone, and your number will still be on Verizon, and you won't have this huge hassle of having to port back.
If you ARE happy, then you just call up AT&T on the 9th, and ask them to port your Verizon number onto you existing AT&T line. When you do that, the Verizon account will cancel, the number AT&T gave you will go away, and your old Verizon phone number will transfer to your iPhone.
Technically, the one drawback to this is you'll be paying for service on two carriers between now and the 9th. However, most ports work in such a way that the carrier you're leaving gets to keep the full month of service you paid for anyway, even if you port out in the middle of the billing cycle. So, it's a wash anyway, and you may as well use this time to your advantage.
By the way: be careful with when and how you port. Make sure that Verizon will release you on the 9th without an ETF. At the same time, don't wait TOO long after the 9th, or Verizon will get you for an additional full month of service, even though you ported early into the next billing cycle. The porting regs let them do this, and since you're leaving anyway, Verizon isn't really going to bend over backwards to give you a credit on the unused portion of your monthly bill.
My other question is, my wife may switch to an iPhone in the future. If she does decide to do this, can I have her use it and get the new one at the discounted price or do I have to pay full price?
If you're opening new lines of service with AT&T, then you pay the discounted price. If you or your wife wife already has an AT&T line and isn't eligible for an upgrade, then that line will have to pay full price to get an iPhone.