Not all of the time, but when I'm able, I normally give to them. I can sympathize with most of them, and I can weed out the ones who are just trying to get a quick fix or a drink.
No, they're usually not even beggars. I've seen one pull an iPhone out of his pocket
My friend does tho. She told me that she was shopping in Milan's most fashionable area, when she suddenly saw a clochard, so she gave him €20 ($27), and "felt poor in second person". I was like
Umm no. This homeless kid asked for a meal at my aunt's restaurant so we gave him one for free & he thanked us by stealing the silverware and salt & pepper shakers.
Random people begging on the street? Only in extremely special circumstances.
Generally, no. I'm not paying for someone's drinking/smoking habit. I've seen enough to know better than to just freely give someone on the street money.
No, they're usually not even beggars. I've seen one pull an iPhone out of his pocket
My friend does tho. She told me that she was shopping in Milan's most fashionable area, when she suddenly saw a clochard, so she gave him €20 ($27), and "felt poor in second person". I was like
In Via Montenapoleone?
I have never seen beggars in upscale streets or neighbourhoods. But yeah, you are right.