From deductions to IRAs, our experts answer your questions

Now that we've rung in 2010, it's time to think about our fiscal health. And with tax season only four months away, the sooner you get started, the less panicked and stressed out you'll be. After all, isn't one of your New Year's resolutions to reduce stress in your life? Our experts tackle two such questions to help you get started.

Question:

I sold stock at a $15,000 long-term loss in 2009. I never have enough deductions for the long form itemization but was told that I couldn't deduct the losses. I have some long-term gains that could be sold. How much loss can I take a year? How much gains can I sell? Can I itemize if, say I take $10,000 in gains and offset $10,000 in losses and carry over $5,000 into next year?
-- Corbett