As far as the quest dialog - finish any other misc favor quests you currently have. NPCs generally won't offer you a favor quest (that's what these kind of side quests are) if you already have any similar ones active.
In regard to him missing the vendor dialog line - wait for 24 hours and try to notice what time the day changes over. If its nowhere near midnight that means your daily clock and date-change are out of sync which can cause scheduling problems with NPCs - ie they won't open shop at the proper time.
Are you on the PC or a console? There's an easy fix for that time/date sync problem if you are on the pc.