If it hasn't
recently snowed a decent amount when Dec 30th rolls around, the conditions most likely will be seriously icy. This is a pretty dangerous route. A professional guide
with an ice axe and crampons died on the route a few years ago ('04). Last winter, a marine from 29 Palms fell
800 feet after slipping on ice. By some miracle of God, he wasn't killed.
For your first time on the "trail," you might consider a) only going to the tram (instead of all the way to the peak) and, more importantly, b) doing it in clear, dry (no snow, no ice) conditions. The "trail" is indistinct in places, there are a lot of false trails, and people commonly get disoriented. Get familiar with the "trail" in good conditions for your first time, and perhaps then try it in tougher conditons.
Now if you're an experienced winter traveller with lots of time under your belt using an ice axe and crampons and navigation in snow country is second nature to you, then perhaps what I'm saying doesn't completely apply, but do be careful.
If you do decide to go for your first time in decent conditions, you may not want to wait until summer. It gets so hot, 110+ isn't unusual, that heat exhaustion becomes a very real possibility. April would probably be a good month. The days will be longer, the temparatures more moderate, and (depending on whether we have a wet winter or a dry winter) the snow will likely be gone or at least not an impediment to travel.
By the way, I completely understand about the "itch." I sprained my left knee about three weeks ago. There's fresh snow on the mountains right now. My skis are in the closet whining like a puppy dog when you're about to leave and you're not taking him.
Believe me, I know what the "itch" feels like. Just don't let the "itch" cloud your judgement.
Peace bro' and happy trails.
P.S. Perry, who runs this site has a lot of helpful info on the route at
http://www.geocities.com/cactus2clouds/skyline.html