The quest is a bit weird. In order for him to want to give you the quest, you have to have walked over the trigger outside the door. Especially when not coming from the boat, you don't always walk over the trigger.
The easy fix should be to just walk around outside a bit until your journal is updated. Especially a bit to the east of the shop.
Basically it is the way NWN quests work, and I can guess the way that quest was made. It checks whether you already started the quest (by walking over the trigger). If not, it checks whether you have a certain progress, and whethere you are finished with it. If neither of these are done, NWN doesn't know which conversation to give you, and gives you none at all.
Of course, I might be wrong, but I think I ran into this problem once as well.
I had this happen to me today. I walked over the trigger, and got a blank named quest in my log. Pickering wouldnt talk to me. I went across the street, talked to the fletcher, then walked back over. The trigger didnt pop again, but it did let me talk to pickering and start the quest.
Okay, I made the trigger a bit larger, but technically your PC wouldn't know about the quest until (s)he actually walked into the ally that Speedy's Courier Service is in. It's easy to 'know' about it as a PC and go straight to the first NPC, but the quest actually starts with the trigger outside Speedy's that mentions the courier almost knocking you over.
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