I used to work in Downtown Orlando, which is notorious for its amount of people walking the streets no matter if it's day or night. I worked Downtown for about six months, and I started to notice the people who were peddling every day, as well as people who were truly homeless sleeping outside my office building. After a while, it started to get uncomfortable walking around town on my breaks or time off. It got to a point where I couldn't even use headphones because I had to listen to the environment around me.
Here is some clarity into one situation I was in:
In one situation, a person stood right in the exit of the parking lot (one way in/out) and wouldn't move until I answered him (he was asking for money). I couldn't drive away until he moved out of the way, and I didn't want to make a big deal out of anything.
I am not saying one should treat the homeless in a different manner - and I find it very keen to listen to what's around me, otherwise, you're going to get hurt or something pickpocketed from you.
What is the best way to handle a difficult encounter with someone who is truly homeless - and also other situations with people who aren't homeless?