Regarding upgrades as a Gold: I THINK I'm getting them b/c I'm open to dates, book within days of my trip and yes, am booking higher fares. That is mostly due to my last-minute travel. I'm basing my stats on 2014.

When I book, I can SEE that flights through ORD are cheaper, but they're less miles and that is a VERY difficult UG. I rarely buy up at the kiosk (it'd have to be one long flight!) b/c I don't LIKE those offers going to people. I'd rather sit in economy than encourage the company to sell those last-minute seats instead of UG. I know I did it when I had a kidney stone on a return flight, but that was IMO necessary. If I'm going to pay MORE for a ticket I'll do it at original purchase and get the extra miles out of doing so. But again, this is SO rare- having purchased months ahead, I wasn't able to see the upgrade list or know what it'd be like this close to leaving.

If I could be sure of getting all our luggage in, I would've done 2 separate reservations. It's also confusing that when signing in under my hubby's FF number or my son's, neither one Premier, I see it state that there are no charges for 2 bags each. I know this is b/c they're sharing a confirmation number with me, but it could've been taken as it read! I'm so glad I asked before I did something stupid. And I can understand WHY the 2 reps had different answers for me. It IS confusing!

Thanks again for the help!