John Schaaf

If you have a family member with low income, they may be able to pay no Federal tax when selling stock that has been held for over 1 year.  Assume you have a 25 year old child with little income and you have a large gain in a stock or security you hold.  Instead of selling the stock, paying tax on it, and giving the child money, consider gifting the appreciated stock or security to your child and having them sell it.  If you do, your child might be able to sell the stock, and recognize the...

Assume you bought a stock for $5K that has appreciated to $30K.  If you sell the stock and donate $30K to charity, then you have to recognize $25K of gain and might be able to deduct some or all of the $30K if you itemize.  Instead of selling the stock and donating cash, consider donating the stock to charity and telling them to sell it to generate the cash they need.  If you do, then you don’t recognize any of the gain and still might be able to deduct some or all of the $30K if you itemize.

You can pay no Federal tax on the gain recognized from the sale of stocks and securities held for over 1 year to the extent you make less than around $124K as a married couple this year.  So, if you are married and have joint income of $100K this year, you can sell stocks and recognize long-term capital gain of around $24K and pay no Federal tax on it.  Any gain over $24K would be taxed for Federal purposes.  When consider taking advantage of this, be aware that the extra income from the...