Has anyone been able to get AT&T do a 2 year contract extension slightly early? Like a few weeks? I'm a 10 year customer and should be able to get a regular upgrade (don't want to move to next, pay 62$ month for 500/rolly, 200 sms and unlimited data) but would rather get my phone before 11/19/14, my regular upgrade date? Any leeway here?
In a word, absolutely. These contracts that everyone seems to be so afraid of or concerned about are not written in stone. In some cases, the ETFs are waived entirely, but one thing you have to do is to be proactive. Call customer service and simply TALK to them. If you get a rancid individual that can't be reasoned with, don't get upset or into an upsetting argument. Instead, hang up, and re-dial 611. If everything seems to go south even after your best attempt, tell them you want the retention dept. There, you might also want to drop the name T-Mobile and that you've seen their incredible offers, but that you'd really like to stay with AT&T.
One more thing, and this is important: Never be rude. Nobody wants to do favors for someone who's obnoxious or rude. Always be courteous. You can register your disappointment without flying off the handle, if you don't succeed at first.
Alternatively, although in your case, I certainly don't recommend it since you're so close to your contract end date, is to do a 1-year upgrade extension. This will not give you the full subsidy, but it will give you $200 off (instead of $450 for 2-year contract renewals) the full price of the phone. This is what I've been doing every year since the 3GS. Of course, you can further offset the upgrade price by first unlocking your existing device (AT&T will do it for free if you upgrade!) and then selling it. Apple products are the very best at retaining their value.
Hope this helps! ;-)