Reddit mentions of Step by Step: Basic Buddhist Meditations

If someone you know will use the money for something that hurts themselves or others, you don't need to give them, but it's usually not possible to know what a homeless person will do with the money, so it may be best to give it with the intention to help them and do so in a respectful manner.

"The second impure motivation is lack of respect.... Yet sometimes we forget to show respect to those who ask for help. We may look down on them or humiliate them, or we may be tempted to think how great we are and feel proud. If we want to practice generosity purely, then this kind of attitude must be abandoned. Bodhisattvas always regard those who come to beg for any material help from them as their great spiritual master and show enormous respect.... Another important thing to be aware of is the purpose of giving help. What this means is that we should thoroughly check on whether the help we give is going to harm others. Sometimes our motivation may be correct from our side and we feel no miserliness toward our possessions, but unskillful giving of help can sometimes harm others.

... The third wrong motivation is expectation. If we sincerely want to practice the perfection of generosity, then it is very important for us to try not to have any expectations. The kind of attitude we should generate is that we should regard those we are helping as our great spiritual master, regardless of whether they are highly realized persons or deluded ones, poor or rich. We should show them great respect and must make sure that our motivation is really to benefit them and not expect any kind of reward." – Geshe Namgyal Wangchen https://www.amazon.com/Step-Basic-Buddhist-Meditations/dp/0861716000

Karma is intentional action: “when you do something without intention, such as killing insects without knowing it... you do not accumulate the karma of killing.” Obviously, giving with the intent to hurt someone, such as giving them poison or drugs that they'll overdose on, is bad karma. Three impure motivations:

> The first is giving material help to other but with bad intent...

> The second impure motivation is lack of respect. When we give material help to others, our intention might not be to harm them but genuinely to help. Yet sometimes we forget to show respect to those who ask for help. We may look down on them or humiliate them, or we may be tempted to think how great we are and feel proud. If we want to practice generosity purely, then this kind of attitude must be abandoned. Bodhisattvas always regard those who come to beg for any material help from them as their great spiritual master and show enormous respect.… Another important thing to be aware of is the purpose of giving help. What this means is that we should thoroughly check on whether the help we give is going to harm others. Sometimes our motivation may be correct from our side and we feel no miserliness toward our possessions, but unskillful giving of help can sometimes harm others.

> The third wrong motivation is expectation. If we sincerely want to practice the perfection of generosity, then it is very important for us to try not to have any expectations. The kind of attitude we should generate is that we should regard those we are helping as our great spiritual master, regardless of whether they are highly realized persons or deluded ones, poor or rich. We should show them great respect and must make sure that our motivation is really to benefit them and not expect any kind of reward.

If a guy asks for money to buy cocaine, we should not help him:

> Another important thing to be aware of is the purpose of giving help. What this means is that we should thoroughly check on whether the help we give is going to harm others. Sometimes our motivation may be correct from our side and we feel no miserliness toward our possessions, but unskillful giving of help can sometimes harm others.

https://www.amazon.com/Step-Basic-Buddhist-Meditations/dp/0861716000