One point of order:
- Ms. Burch is Ashly, without the 'e'.
- Ms. Johnson is Ashley, with the 'e'.
Second: I assume most know about Talks Machina, their 'after-show'. If you care enough to invest the hour to watch it, it can be revelatory, particularly when something dramatic happens about which there are questions.
As to the specifics of the OP:
It seems the recap posts have stopped else I would have posted this as a comment there.
But I have a couple of things I'd like to discuss about the episode, so expect spoilers!
Thing #1 - Keg's rolling at disadvantage. I felt like this kind of blindsided the group and was not necessarily foreshadowed enough. Perhaps I missed it in the lead up - but I do think Keg should have been a lot more trepidatious about the encounter so that her immediate panic would have made more sense in context. I also think Ashley should have made Keg at least attempt to overcome her fear by making a charisma save (perhaps DC 20 to illustrate how hard it is for her character to overcome her fear). Making her frightened by fiat made it seem more of a screwjob. (Note: I don't want to make this into a pile on to Ashley. I thought she was a fun player that participated with gusto.
I'm more interested in how others might have handled that development).
Link to the relevant bit:
https://youtu.be/BXFTboNHtE8?list=PL7atuZxmT955Cw-fFS-_3IQvaCpQgDzWA&t=15720
Handled as a player or as a DM? (All your commentary here seems to be about what Ashly did, but most of the subsequent discussion seems to be focused on the DM response.)
As a player, I'm not sure I can say, since I'm not sure I would have thought of doing what Ashly did. As far as foreshadowing goes, I'm guessing
Ashly didn't think in advance about how Keg would react to being in combat with Lorenzo, and I'm willing to take that as representing that
Keg didn't really think that far ahead either. It is not uncommon for people to react differently to the reality of a circumstance very differently than they do to the anticipation of that circumstance.
As a DM, if the players were like the CR cast, I would do pretty much what Matt did - go with the suggestion. If the players were more like
my players, I would have a short conversation with the player to understand what they were really trying to get at, but I would probably end up in the position - ok, I'll take account of what you are telling me about your character's mental state, but you just tell me what you do and I will decide on the mechanics. The mechanics decision would depend on the particulars of the case.
Thing #2 - Molly's death. Did I miss it or were there no death saving throws made? Matt just said "Molly's dead" and that was it? Is this a homebrew rule? I have to think that this was pre-arranged (at least the possibility, and acceptability, was agreed upon before the session), otherwise this characters death was quite perfunctory.
Link to the relevant bit:
https://youtu.be/BXFTboNHtE8?list=PL7atuZxmT955Cw-fFS-_3IQvaCpQgDzWA&t=16631
The matter of the death saving throws has been pretty well addressed. As to the death being pre-arranged, I don't see any evidence of that in the stream, and what was said on the subsequent Talks Machina made it quite clear that it was quite unexpected by Taliesin. And in fact that the death was 'perfunctory' as you say seems to me to weigh heavily
against it being pre-arranged. I mean, if you were going to arrange it, wouldn't you arrange to make it a bit more heroic?
As to the details, I will add that Matt did say that Lorenzo was going to make two glaive strikes on Molly and made two dice rolls, but he skipped his usual practice of announcing what he rolled. Also he usually asks the player either what the PC's AC is, or if the announced roll hits and he didn't do that either. That departure certainly confused me in the moment - I had to rewatch the sequence to see that he actually did roll the dice. So I can understand being left with the sense that Matt just narrated the death, but that is not what really happened.
My speculation: AFAIK, Matt relies on the players to track their HP. So when he announced Lorenzo's intentions, probably all he knew was that Molly was hurt and might get knocked down. In the course of 12 real-time seconds, Molly knocked himself out and Matt rolled two numbers that he knew were hits, which changed the situation to Molly is dead. At that point, I think Matt was just trying to focus on finding an at least somewhat meaningful narration and figuring out whether Lorenzo was going kill them all.
Thing #3 - Not a TPK. Given how on the ropes the party was it could have easily ended as a TPK. Matt dialed it back and made them witnesses to Lorenzo's brutality. Which is fine and well within the DMs purview. But it also supports my theory that Molly's death was pre-planned - otherwise Taleisin would feel even more screwed over (he could have been added to the prisoners instead).
Link to the relevant bit:
https://youtu.be/BXFTboNHtE8?list=PL7atuZxmT955Cw-fFS-_3IQvaCpQgDzWA&t=17536
My biggest puzzlement is Thing #2. That seemed quite strange!
Edit: added links to the parts in question
On TM, Matt said that without Keg stepping in, any of the M9 that did not flee would have died, even if that meant a TPK. I think it is a fair speculation that at least subconsciously Matt was probably 'very open' to the remaining party members finding a plausible way to survive, and Ashly provided one.
At the time, Lorenzo thought he was full up with prisoners (mentioned in the abduction scene in previous episode), not realizing he had just flash-frozen three of them (oops).
I think Taliesin was sad and upset, but not in the sense of feeling screwed. Molly was very much a part of his own undoing.