I hear what you are saying and generally agree. I remember in the 90's when I used to take the bus from the airport to Negril I most hated the drive through the streets of Lucea where I found myself looking out the bus window staring at poor people who were just staring right back at me. I just couldn't take that. Now when I travel in Jamaica, I stop off at places were obviously poor people live and work and spend a little money here and there but I don't "hand out $$" as that just sends the wrong signal. When I get asked for money sometimes I just ask back, "What are you willing to do for the money?" Usually I get this blank look and I continue, "I worked for my money, are you willing to work for yours?" Picking up plastic bottles, trash, etc. are some things I am willing to part with a couple of hundred Jamaican for. Doesn't have to be much but just showing the effort makes us both feel better about the transaction. Most don't want to beg.
If you do go back, get off the bus and mingle. A few gentle "No"'s go a long way to discourage and it gives you a moment to educate people on the proper way to interact with visitors. I live in an area where most of the time I am the only "tourist" within say 20 miles or so. I operate off of Respect. It is a two-way street with me. The more they see I am just like them and I Respect them, the more Respect they show for me. I love my little town. http://www.accompongtown.com
Respect.