SRQ Guy,

Are both of you Silvers now? If yes, AND you have enough upgrade points in your Skymiles account AND you book some K fares or above for this Turkey Day weekend, you probably won't have too much trouble upgrading. (providing you call in exactly 24 hours before the flight) I'm not sure if you could request the upgrade in advance; yes the website has that option, but it doesn't work for my itinerary (even though it was booked in K).

When you call DL that 24 hr before the flight, ask for an upgrade to all segments, depending on how many upgrade points you want to spend (1 upgrade point is good for 800 miles; and it's by segment only, so a minimum of 1 point per segment)

Now, if you're not yet a Silver, I wouldn't know how you would be able to upgrade except for using miles from your account. (i.e the above won't work for you)

After you make Silver, you could do the same thing for your Christmastime travel.

I'm not sure if that's what you're asking, or if you need more specific answers, please let us know.

Hope it helps!
Jamester