John Schaaf

Effective Dec. 24, 2025, USPS will define the postmark date as the date of first automated processing, which may be later than the drop-off date. Because tax filings are considered timely only if postmarked on or before the due date under IRC §7502, taxpayers should mail documents at least two days early or obtain a manual postmark at a USPS retail counter, or use Certified or Registered Mail. For example, dropping mail in a box at noon on the 15th could result in a postmark of the 16th if it...

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.