This is an important post, and I'm fortunate I happened upon it. I read back to the beginning of this particular topic, and read ( and bookmarked, as Savannah did ) your blog post Fishy. I have thought about this many times over the years.
When I am feeling well and healthy, I hold the doors for everyone. Children, men, women, aliens etc. My parents taught me to be considerate of everyone, ( not so much myself though, but I digress ) There were times when I wasn't well, I would have been very grateful if someone had held open a door for me... that's when those big handicapped buttons were great!!
The times I didn't know what to do, was when someone was in a wheelchair. I decided a long time ago to ask, would you like help, and always make eye contact. If the person said no, I smiled and went on my way. Now... please tell me, is this hurtful, because I'm still questioning the person's ability to be self reliant.
As for homeless individuals, I give every person that is panhandling something. Personally, I never do this without making eye contact, and saying a few words....if the other person is comfortable. There are all the arguments that the money will be used for drugs, drink etc. but hell, it is a small gift, one I'd hope would be passed to me if I had need.
Before I had children, I didn't hold these views. I have major depression, and a child with severe mental illness. That person on the street could someday be me or my child. Until we experience things ourselves, it is sometimes difficult to understand. It's great to have this place to share and learn.