As long as you aren't giving them money to piss away on drugs or something similar, so what? You would give your family and/or friends an easier and happier life.
Maybe, but be careful. It doesn't have to be drugs. You can cover their food and some of their house payment, because they're broke, but they bought a new boat (or similar expensive item) anyways. Surely, they can't ask their rich relative for too many vacations, right? Or vacation houses?
For someone who keeps their word and is honest about their finances and asks for such-and-such, fine. For those who don't care for paying off the debt they have and always gets more, and you give them money, you're feeding their entitlement, and ultimately making no one happy.
