I'm really bad for feeling guilty. I had a thread on here before about some 'homeless' guy pestering me for money. To cut a long story short, he begged me to go to the atm to give him money for a place to stay - bear it in mind it's really dark - then asked me to walk with him to the hostel. I freaked out, gave him a few quid and got the hell out of there, stopping at the hostel on the way to pay for his stay, incase he was legit. As it turned out, they stay because of the council, and don't take money.
As you can probably guess, I'm generally walked over when it comes to people on the street asking me for x.y&z. I will no longer be any sort of doormat.
In my case, it rarely happens to me, if ever. I can't really trust them. They're probably not "homeless" but alcoholics, drug addicts, lazy people, etc. Or liars. Although that's not the only reason I ignore them. It's not like we're forced to give money to whoever asks us.
My mother told me once she noticed a FREAKING LIMOUSINE taking a supposedly 'homeless' man to who knows where. It was something that happened every day. Why were they doing that? I have no idea. But it does seem really suspicious.
I’ve had my land line for 7 years now. For at least 4 of them, I got constant calls for a Deborah Blume. She apparently owed a lot of people money or something. I told everyone who called they had the wrong number. I still will get the occasional call. I put myself on the no call list and that helped a lot.