Just before and just after my son Clark's birth, I had several  encounters with strangers that left me wondering what I should or would do  in a similar situation in the future.  There were three encounters and  each involved a vagrant or panhandler.
The first  incident occurred a few weeks before Clark's birth.  Clark's Mom and I  were walking down the Las Vegas strip on a warm Spring Sunday morning.  Clark's mom was obviously showing at 9 months  pregnant.  She was wearing a custom t-shirt with our last name on the front and mommy on the back with a number like  a softball jersey.  We walked pass a woman on the sidewalk with her young  daughter beside her.  She was holding a sign (with wording I can't  remember) and panhandling.  
My wife was greatly disturbed by the  encounter. She told me that she felt bad flaunting her pregnancy with the t-shirt, while another woman was so desperate as to panhandle with here child at her side. I found the  child being involved distasteful.  It didn't really bother me too much, as there was no direct contact and we had passed a number of other panhandlers on our walk. 
Mere  hours before Clark was born, my wife, in early labor, and I visited a  certain big box retailer - O.K. "The Big Box retailer."  We were finishing  last minute (literally) preparation of the nursery. As we exited the car,  we were approached by a young woman holding a little girl. She then said, "Can i ask  you a question?"  Coming from a stranger, I knew this conversation was not heading anywhere positive.  The question was, "Could I spare $5?" 

 
 The "Big Box Store" was in a pretty nice neighborhood,  but starting at $5 was pretty ballsy for a panhandler.  They normally  ask for spare change or maybe a dollar.  I responded that I didn't have any  cash on me (because I don't usually carry any).  She then went on to  solicit others in the parking lot.  As she walked away, I could hear the  little girl had a bad hacking cough, but that's not what the woman was requesting assistance for.  It probably should have been.  I felt very bad for the  little girl.  Admittedly, being directly accosted made the  situation feel more personal.