There are several ways to get good deals.
End of season sales are an excellent time to buy demos. Shops and resorts don't want them hanging around all summer.
At the end of summer/early fall, you'll usually find lots of sales to move out whatever is left of last year's gear and apparel. As you get closer to the season, anything from the previous season gets scarcer, so the earlier you start looking, the better. If you want this season's stuff and your local shop is out of your size, they can usually order it for you.
I recommend getting yourself on the mailing lists of nearby ski shops so you get notices of their sales.
Also, I believe you mentioned a ski trip in January to Breck. Believe it or not, lots of resort-area shops have sales in January. You could very well find an excellent deal while on vacation. How cool would that be? ;)
Ski swaps are an excellent resource. Many people use their gear for a year or two and then HAVE to buy what's the latest and greatest, so they sell their gear at swaps for cheapo prices. That's how I have a "quiver" of skis.
Some swaps are definitely better than others. I'm not sure what swaps near you are the "best"--you're in Florida, right?--so you'll have to ask around. Maybe find the website for your nearest ski club. They usually have that kind of info posted (often they are the ones holding the swaps, but also look for ones sponsored by schools and ski shops).
As SnowHot said, online shops are a great resource. In addition to the websites she mentioned, try sierratradingpost.com and altrec.com, both are reputable.
Thatsagirl