Once I went to Wendy's, and a bum met me outside the door. He said I looked well-dressed and started chatting me up. Following me inside, he said he was hungry and just wanted a couple bucks to get some chicken nuggets. I was a sucker and gave him a couple bucks. Then he asked someone else for a little bit more to get a meal or something. Once he got his cash, he hurried outside and ran across the street to the liquor store, without ordering his chicken nuggets. Really changed my perception of bums.
Just a month or two ago, I was cleaning out my car at a car wash around 10 o'clock at night. Then I saw a dude and his kid - I put him around 9 years old - looking inside all of the vacuum cleaners. I tried not to pay attention to them, and when I look back up, the kid is hanging on my door. I said "hey there" to him and then his dad said "not that one, go on to the next one." When they kept going, I was a little concerned. I asked them if they needed help finding something. The dad said he's just looking for change. A bum is one thing, but making your 9-year-old son dig in vacuum cleaners for change at 10 PM on a school night is just not right.
After my prior bum story, I decided that I wouldn't give a bum anything without finding out his story first. So I did. I asked the dad what was going on. He said he and his son got kicked out of his girlfriend's house and they have nowhere to go. I asked if he tried the local homeless shelter we have in town (we have a really nice one), but he said they were already closed. He said he's disabled and has a metal plate in his arm and can't work for some reason. I didn't buy the not able to work part, and more than pity for him, I was just frustrated that he had provided that kind of life for his kid.
He said they were hungry, so I said I might have a snack or something in my car. I usually do since I have a 2 year old son. Unfortunately, I just had dum dums, so I gave them a few. I went back to cleaning my car, and I felt bad as they continued to dig in the vacuums. I decided to open my wallet, and I just had one dollar on me (I rarely carry much cash). I gave him the dollar and said that was all I had. The dad was pretty excited and said he could go see this lady that sells donuts and get something to eat. Man, I felt bad for the kid. I probably should have driven them to McDonald's or something and used my debit card, but I didn't think about it. Plus you don't want to feed a problem or else it'll never get better.
I told my wife about it when I got home, and she said if a cop had seen them out there then they would have taken the kid away from him. She works with kids and has unfortunately had encounters with DHS before.
To answer the OP, the most I've given a bum is $5 for gas. And I pumped the gas into their car to make sure that's what it went to.
The least I've given a bum is nothing.