It's a fine line between enabling someone to use their personal accountability in destructive ways by giving them assistance that might prolong their bad habits, and emulating how Jesus served and helped and lifted the "kingdom of nobodies" that filled his ministry - a line I struggle to define continually. Personally, I would rather help ten in order to be a "savior" to the one who truly will appreciate that help and use it wisely than to help none and miss that one. Having said that, I also want to find a way to enable as many people as possible to accept their own responsibilities and reach a point where assistance no longer is necessary.
As I said, it's a fine line - but if I can't walk it perfectly, I'd rather err on the side of compassion than judgment. I've been on the receiving end of both, and compassion was better every time.