[DrJonson]

Even if you could afford it ( and its not going to harm you or your family , helping others but making your family and yourself wanting of money is not permitted ) .....
It is part of your ibadah to judge and be sure you are spending your sadaqa in the right place with the right people. Use your other resources given to you by Allah to make that decision ( Intellect ) .

Allah looks at the Intention . If you come to a wrong conclusion while your heart was in the right place Allah forgives . If you give someone the money and have doubts about the person say in your heart Allah forgive me and forgive him if I am wrong .

The Sadaqa is for the sake of Allah .

With Allah every action for the sake of him is profitable

You are a good person .

also is it something he can afford and not miss it (i.e. is it just a little thing to him) or will it make a hole in his pocket?

personally if it is something small I to me I prefer just to give it away and leave it too Allah.

I remember one day a few years ago I was approached three times on the same day in different places by elderly rustic Saudis in banged up cars who were staying in Emirates and were begging for petrol money so they could visit their families for the weekend

at the time I was able to give it too them without it causing me any problem so I just did, it was in my mind well these are nice old men but maybe they do this a lot and they are just saving money so they have more to give to their families etc, but on the other hand I didn't know that for sure, as far as I know they were angels who were sent by Allah to test me..

and anyone who asks you for something could be, this is not just imagination...

anyway what I am trying to say to you mikhal2 is if it is a small or easy amount to you maybe it is just nicer to give it to him and assume that it is important and a good deed?