This directive is mainly to do with caring for the poor and needy amongst the church of God, be they members of your own church fellowship, or of the extended church family. They do exist, their struggles in life often hidden because we only see them for a short period of time on a Saturday or Sunday for example, and then only in passing before or after our fixed agenda meetings (worship services, Bible studies, prayer meetings and the like). How will we get to become intimately aware of the true life situations of our brothers and sisters in the Lord, if we don't have the opportunity and take the time to get to know them properly. The concept that we must have a formal agenda most times we meet, is just plainly counter-productive to quality fellowship.
I fellowshipped at a large church group some time ago, and was astounded by the lack of care, particularly in respect of monetary and relationship support, for the single parents (often struggling to house, feed and clothe themselves and their children), and for the orphans (those that don't have other Christians in their biological family, or are distanced from them, and the like, and are therefore devoid of relational support). Yet we required that they turn up every Sunday etc, obliged them to tithe and participate in the 'show', then sent them home needy and/or lonely.
As Christ followers, if after having met the needs of our own family, and the disadvantaged in the body of Christ, or if we come across a situation similar to that of the 'Good Samaritan' or anyone in need, and we are fairly confident our pearl-like gift won't be trodden on, and we have the wherewithal to give, then of course we should give, and give cheerfully. That's what I must aim to do at least, because I think that's what God requires of me, and I wish to be pleasing to Him in everything.
I wouldn't recommend an individual walk amongst the homeless and the like, offering help. By all means do it as a group, it is a good outreach, but even so be circumspect about how and where you do it. Unless you had a hand in causing a homeless situation, you are not responsible for it. In truth, the government and NGOs are often better placed to provide qualified support for those in the outside community that are homeless, as they have the resources and expertise to deal with what can be very complex and problematic situations.