This is a really difficult balancing act. It's hard to see people, especially people we care about, struggling with a situation when we know we could either help or make the entire situation go away.
Help with too many conditions can become controlling; help with too few conditions can become enabling.
I think a lot of it comes down to what kind of help will best address the situation.
I think of a couple I knew a few years ago who were constantly short of money. Offering them money to get them through a tough spot wouldn't actually help because they'd be in the exact same situation next month, and the next month, and the next month. Their budget was fundamentally broken because of foolish spending patterns, so what they really needed was someone to help them adjust their spending. But their most foolish spending pattern was non-negotiable to them, so any financial help would be dumping money into a bottomless hole.
If people are willing to do the work to resolve their problems I'm usually happy to help them. If they just want a quick fix then I'm less interested. The only exception to that would be that if someone who is very close to me had an immediate and urgent need I'd look to address it first and figure out the details later.