For many people, December is the riskiest month in which to buy into a new mutual fund in a taxable account. This has nothing to do with the gyrations of the stock market, and everything to do with taxes. Read the full article

As the end of the year approaches, it’s always a good idea to take see if there are any last-minute moves that make sense for you. Here are four opportunities for tax savings: Read the full article

At this time of year it’s a good idea to look for last-minute opportunities to minimize your taxes. Most opportunities require some action before the end of the calendar year; here are several ideas to consider. Read the full article

Many employers offer Flexible Spending Accounts (FSAs) that can be used to pay for healthcare expenses not covered by health insurance. If you participate in one, the money that you have withheld in the account has use-it-or-lose-it status. In some plans, the deadline for spending funds contributed in 2008 was 12-31-08, but many plans have taken advantage of an IRS provision that allows prior-year FSA funds to be used up to 2.5 months after yearend. The deadline this year is March 16th (the 15th is a Sunday).

FSA funds can be used to pay for co-payments, deductibles, or other expenses not covered by your health insurance. In addition to prescription drugs, the IRS has ruled that FSA funds can be used for certain over-the-counter medications.

A number of online over-the-counter drug vendors provide information at their sites regarding which medicines qualify as FSA-reimbursable expenses. Medications for acne, cold medications, pain relievers, and a wide variety of other items can be purchased to use up remaining funds in your account (the IRS frowns on “stockpiling,” though, so don’t buy thirty bottles of Beano®). Be sure to maintain receipts showing the items purchased so that you can substantiate the eligibility of your expenses.

Any funds not used by the deadline are lost to you, so if you’re not sure when your FSA’s deadline is and you have money left from last year's funds, check to be certain. Read the full article

The Emergency Economic Stabilization Act of 2008 (a.k.a. “the Bailout Bill”) changed the reporting requirements for annual tax statements from brokers. Form 1099-B, which formerly had to be sent by January 31, is now due on February 17 this year (the statutory date is February 15, but in 2009 that's a Sunday and the 16th is Presidents' Day). Read the full article

I’ve already written elsewhere about year-end tax minimization strategies. With a little more than a week left in 2008, time is drawing short for carrying out many of them. Here's something you still have time to do: charitable giving. Read the full article

With stock markets down precipitously and few asset classes that haven’t declined significantly this year, many investors in 529 college savings plans are wondering what to do. In some situations, it may make sense to make a change in your child’s 529 plan. Read the full article

In my earlier post on Roth IRA conversions, I noted that if you converted an IRA into a Roth earlier this year it may make sense to recharacterize the funds if the value of your account has slumped and you still owe taxes on the earlier, larger conversion amount. I also stated that you can’t go back this year and do another conversion. However, I realized that there is a way to sort of do a conversion/recharacterization/reconversion. Read the full article

As 2008 draws to a close, take some time to consider what you can do before year-end to reduce your income tax bill. Read the full article

With stock market indices down 30% or more from their January 1st levels, most investors are battered, bruised, and hoping for happier times. In the midst of a generally depressed stock market, there are still a couple of clever ways to make the most of a bad situation using a Roth IRA. Read the full article

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