When I'm looking for a person to give a package to, I try to spot the ones that look like they're in the roughest shape. If they want to, I'll spend time just shooting the breeze with them.
While they're certainly appreciative of the gift, I have very frequently heard two things from them: the main thing is that they really appreciate someone treating them like a human being rather than ignoring them or treating them like garbage. And they also really appreciate someone just having a chat with them.
I think lots of people tend to objectify the homeless, to think of them as somehow less than, or fundamentally different from, "decent society". The truth is that they're not. Any of us is just a disaster or two away from joining their ranks.
EDIT: I just wanted to add one anecdote (of several) to highlight my point. One day when I was making my rounds, I spotted a man who didn't look particularly homeless in appearance. He had clean clothes in good repair, reasonably well-groomed, etc. But over the years I seem to have developed a kind of "sixth sense" and asked him if he was homeless.
He told me that he'd been on the street for about a week. A few months earlier, he had an excellent professional job, plenty of money in the bank, owned a house, and generally had everything that people strive for. Then he suffered through a bitter divorce that ended up with him stripped of everything, leaving him broke and homeless. There was nothing obviously wrong with him -- he didn't seem to have a serious drug problem or crippling mental/emotional issues. He could have been any of us.
(I gave him a care package and some advice: to make it his priority to get off the street as quickly as possible. If he stays homeless for more than a couple of weeks, he's likely to remain there for years, maybe forever. My care packages include a list of where to get help and resources of various sorts, so I pointed out one that is particularly suited to his situation and strongly encouraged him to go to them. I hope that he did. I never saw him again, so I think he may have.)