Here's something a friend told me that I think is helpful - figure out their personal yield on the stocks. This goes with the whole cost basis thing as well. Set up a spreadsheet with the stock, the share price on date of death(easily googled along with the other option on valuation), # shares, current dividend yield and personal yield. be sure it's saved all over the place(in fact googledocs could be a good option.I second the review of their overall financial plan.In terms of risk, if they are being honest about their risk tolerance, respect it. OTOH, If they could tolerate a 10% loss, put in stops to effect that. "Some money" is not specific enough to give particularly good advice. 10K is different than 100K.