What If We Think We're Helping But We're Not

One thing has been bothering me lately. There's been a young man in my little town, hanging around petrol stations and mall entrances asking for money. This young man is dressed shabbily and while he seems generally harmless, does harass people quite a bit for money. From what I've heard, the petrol stations call the cops on him as he makes customers feel wary about leaving their cars when they walk away to pay.
I was really unsure about writing this post as I haven't had this discussion with anyone else other than my husband; I really haven't got the slightest idea where other people stand. But I will write it anyway and cross my fingers that my humble opinion will be read and respected as everyone's should, whether there be agreement or disagreement.
This young man isn't the only person I have come across. There is another homeless man (let's call him Bill) whom we gladly chat to everytime we see him. He used to hang around our church and ask for money too. I have no problems with these people. What I do have a little problem with though, is people handing them cash thinking they are doing a good deed.
I obviously don't know for sure what they do with the cash and any guesses I have can be easily dismissed by claims of stereotypical bias, shallow accusations and so on. But the next time you get approached, how about offer to buy them a meal if they are hungry or offer to buy them a pair of shoes/coat from the shops/thrift shop if they say they are in need of something?
My husband and I had this discussion ages ago when we were living in a rather notorious part of Sydney and quite often encountered this. It was actually my husband's uncle who told us never to give out cash like that because many times, we might end up doing more harm than good.
Truth is, everytime we have been asked for money with claims of starvation etc, we have offered a meal or a coat (since this usually happens near a mall/shops) but have always been rejected.
And I might add, it is not usually a polite rejection. It is usually a rude frustration with not getting the exact thing they are after - cash.
I hope nothing along the line of judging these people or not helping them comes across in these words because there really is none of that. I have worked with a lot of these people in my previous profession and I do have a heart for them. My husband and I actually enjoy chatting to Bill when we see him. He has a story of his own and is actually a very knowledgeable and educated person.
I think it is great that people have a heart to lend these people a helping hand. Sometimes, though, helping them get out of the situation they are in takes a lot more than simply handing them a $20 note and that cash might actually end up doing them more harm than good. There are many other ways to help and I know this sounds a bit cheesy and might be an occupational habit, but there are many organizations available to help and sometimes we could help by pointing them to the availability of relevant services.
Linking up with the lovely people over at Essentially Jess for our weekly IBOT gatherings :)