You should be alright with leave. I'm in VT-27 and almost all of us are taking off on friday night, the 16th. It'll cost you the two days of leave for saturday and sunday, but that should easily be approved.
I'm not sure what the wait is now, but most of us classed up the friday we arrived, or the following friday. So, I wouldn't expect anything more than a couple week's wait.
If you class up in VT-27 or VT-28 by the 16th, (looks like you might make it). Then absolutely, your leave chit will be approved, we're almost all leaving for christmas, no watch responsibilities. If you're still attached to Trawing 4, my hunch is that there are plenty of married guys not leaving town to fill the limited watch billets available. But, I'm not with the Trawing 4 stash anymore, I don't know for sure.