Is it worth it to upgrade, and what's the best way to do it?
My husband and I and our 2 kids will be flying PHL>ATL>CUN RT in June. We usually pack pretty lightly, but we'll be there over 2 weeks so there is no way we can avoid checking a bag or 2. I am debating having my husband upgrade to business class for the checked bags primarily, but it would also be a nice birthday treat for him as we've never flown in any premium cabin before. I don't want to upgrade all of us as it would be a waste on the kids, and I wouldn't really be able to enjoy the free drinks anyway.
Since we have a layover, would the upgrade cover both flights? I searched the forum, it looked like I could expect to pay $99 for the upgrade. Can anyone confirm? The first flight back is operated by SWA, but the second is AirTran. Would we need to pay for bags on the way back? If hubby flew business on the way back, do you get anything extra on the southwest flight?
If we upgrade, is it pretty easy to use points for last minute upgrades? I have a good amount of RR miles I could transfer. Most of them are in my account. Can I pay for my husbands upgrade out of my account or would I need to transfer first?