Oy. The "give an inch they'll take a mile" seems to really apply here.
I don't buy people stuff or give money (other than for a service agreed upon), ever. Well, not if I don't know them really well, then it's more of a friendly thing that gets reciprocated.
Once I was with a driver at Juici in Negril picking up a whole bunch of patties for a wedding after party. As I'm waiting for them to box them up I step outside and a guy asks me for a cigarette. If you smoke, and I used to, you generally DO give them to each other, it's a polite smoker thing. But my driver, who I have known for some time, came out and yelled at the guy, and told me I shouldn't have given him one because it will make him think to bug every tourist he sees. I wasn't taking it back at that point but his point was understood.
I also rarely stay in one area very long, and so would probably have left Drapers when Dave was still in his helpful phase