So first the bug, when I found Spike and Wyll started getting all huffy with him, I tried using Intimidation on Spike but it would never let me roll the die. I ultimately had to choose a different dialog option to proceed. It would show the die and teasingly shake it, but no attempt to roll would work.

So, feedback. In the course of clearing out the goblin stronghold, I did a couple long rests where Wyll gave background on losing the eye and Spike's role in that as well as that being how he got his Warlock Pact. Thing is, the two convos were pretty similar, just varying on the focus and details and really would have worked better as one combined discussion I think. At the end of each, he basically swore vengeance on Spike. But, at that point we had already met and offed Spike so at the end of each, I was kind of wishing for a 'you remember he's dead, right?' dialog to be offered. Maybe I was supposed to have these convos with him earlier but that was how it worked out and it just came across oddly. Seems like there needs to be some better triggering of companion conversations or at least alternate versions if they happen after events have passed them by.