Converting a Traditional IRA to a Roth IRA

Question:        With the past and perhaps an impending  further drop in the stock market, does it now make sense to convert my traditional IRA to a Roth IRA? Answer:            The recent stock market drop represents an opportune time to convert an existing...

Navigating the Wash Sale Rules

Question: With the recent stock market decline, does it make sense for me to sell stocks that have decreased in value to create losses for tax purposes and then buy back the same positions? Answer:   If you sell a security at a loss and you in turn repurchase the same...

Tax Planning with Stock Issued to Employees

Question:        I recently accepted a job with a startup company and was given shares of company stock at no cost to me in which I will vest over a period of years.  Do I have to pay tax on the shares I receive? Answer:           As with most employee benefits which...

Tax Planning with Appreciated Assets

Question:        I own a stock portfolio which has appreciated significantly in value over the years. Can I transfer the portfolio to my aged mother and have her transfer it back to me upon her death so I can benefit from a step-up in basis when she dies? Answer:...