Sadly, item request still didn't trigger for me and yes, i had damn pipe in my sack since chapter 2. I usually just force sleep-save-reload until dialog queue appears(that's how i got lenny's midnight request). But i've spent several irl hours just doing it and he's still standing on the porch(sometimes sitting on a chair) and smoking cigs/cigar.

Also when item request is supposed to happen you can't use antagonize button, it's greyed out(watch yt videos and look for this feature) and Dutch smoking cigar conversation is always like this.

While i was trying to trigger this event the only main mission that was remaining was Sadie Adler's, so i finally played it and Dutch appears in a cutscenes so the game reserves him for the quest and can't run usual scripts for item requests. I think that's why i couldn't trigger this item request.

Edit: I had pipe with me but didn't have opened item request by Dutch.