The question I ask many people when they are on a "budget" is:
#1 What is the gun going to be used for?

#2 If it's for personal defense, how much is your life worth?

If the gun is going to be used specifically for plinking/range, the Ruger P85/P89 series guns can still be found for a bargain. Just found one on gunbroker, buy it now for $275. They aren't the most refined guns and they are a little clunky but they do shoot (and much more reliable than the budget guns might I add). If your friend is not willing to consider what you are suggesting to him, you have done all you can to help. Some people insist on learning things the hard way. Good luck.