SRQ Guy,
You automatically get 4 segment upgrades in your account once you make Silver. Now, there were discussions over how long it actually take them to appear in your acct but assume no more than a week, since DL is usually quick in doing these things (unlike UA).
Which means for yout Turkey Day weekend you will have to upgrade using your miles (if you do want to upgrade at all); and do it
now if you haven't. Be aware that you can only miles-upgrade Y, B or M fares. (yes they are pricey, it sucks, I know)
For your Christmastime trip, just do what everyone else would tell you...call them exactly 24 hours in advance and cross your fingers. Tuesday, Wednesday and Saturday flights are usually the easiest, short distance routes too. And, like
Spiff mentioned, out of hubs may be tricky, since the hubs are usually where the elite level people mostly travel to and from. But you never know sometimes tis holiday season. Get on the list if they can't clear you on the phone, and check in early.
Thx
Jamester