What exactly was the plan supposed to be at the hotel?

[Dante]

You're ignoring the clear fact that children in ASoUE are extremely capable, sometimes more so than adults; and Kit was desperate and lacked available volunteers, as per page 42: "I have other errands to perform. While Quigley tries to resolve the situation in the sky, I will try to resolve the situation in the sea, and you'll have to resolve the situation here on land." The Baudelaires weren't truly safe at the hotel, no, but they wouldn't have been any safer anywhere else; and at the hotel, they have a change to participate in a plan that will finally bring all the villains to justice. Their task isn't unreasonable when you think about what Kit and Quigley had to do; merely go around in disguise and observe things. It's a fair cop that it all goes pear-shaped, of course; they never observe J.S. or even lay eyes on the sugar bowl. But the disaster of Dewey's death is as much a failure of the adults around them as it is their own; and it's not like the Baudelaires themselves are ever physically harmed.

For consider that the Baudelaires were unrecognised, even by Olaf's associates, until they took off their disguises, so they were actually doing pretty well; and it's a reasonable argument, too, that Olaf would have been unable to act freely surrounded by so many volunteers and members of the general public, even if a large number of villains were present as well - and so we see that he is arrested shortly after he makes his own appearance in the open.

At the end of the day, though, it seems like many of your questions basically stem from a fundamental disagreement with the logic and atmosphere of the series. Have you ever considered that ASoUE might just not be for you? It's not meant to be realistic.

[Foxy]

Kit also is of the opinion in chapter 2 that the Baudelaires are not children anymore, and indeed they were forced to grow up too fast, especially Sunny. I think Kit really did want them to spy in the hotel, and I think they were fully capable of learning important information. They did figure some things out, albeit too late.

[Optimism is my Phil-osophy]

Dante, something does not have to be realistic to be consistent. ASOUE contains elements that subtly refer to the fantasy that exists in many children's books, but most often do so to parody them. And as much as we try to deny it, there is a climate that there is a concrete plan going on in the hotel. A fragmented plane. Most VFD members do not know all aspects of the plan. But I am sure Daniel Handler knows every aspect of the plan.
So far, my reading has led to the following conclusions, Isandthebooks:
1 - The sugar bowl that arrived brought by the crows is not the sugar bowl that was from Esme.
2 - J.S.'s role was to draw people from the incendiary side to the hotel.
3 - The way to attract greedy people to the hotel was to encourage many people to bring money or valuables to the hotel.
4 - The way to attract people who really wanted the sugar bowl was to spread a story that the sugar bowl was about to come through crows.
5 - The way to attract members of the supreme court was to arrange for a trial to take place at the hotel.

All of these conclusions are relatively easy to see through evidence. The following conclusions are part of my hypothesis:

6: J.S. was the woman who took the sugar bowl from TGG.

7: The real sugar bowl contained a deadly weapon, no worse than the fungus we fear so much, but still quite deadly. I believe it contained a musical instrument capable of controlling TGU.

8. The sugar bowl would be used by J.S. to kill VFD's enemies. Alternatively, Micelium Medusoid could be used. (After all, the woman was in the cave that was full of deadly fungus, and apparently took a sample. According to the conversation between Hal and one of the D brothers, JS could use or sugar the mushrooms to accomplish the mission. But that could cause everyone to eat crows).

9 JS didn't want the Baudelaire siblings to be in the hotel. So she asked Mr. Poe to pick up the kids from the beach at the end of TGG.

10 - JS was the woman with the diving helmet, and Lemony the taxi driver. JS was looking into the ocean to see if TGU was around so that he could summon it.

11 - When JS realized that the Baudelaire children were in the hotel, she aborted the mission. She would do nothing that could endanger those children. So JS hid in the cab of the taxi driver, handed the sugar bowl to Lemony, and Lemony removed the musical instrument inside, preparing to use it. (It was probably a whistle, capable of controlling TGU).

[Dante]

Sept 11, 2019 12:42:35 GMT -5 Optimism is my Phil-osophy said:

Dante, something does not have to be realistic to be consistent.

Yes, Jean Lucio, I know this. I'm just not confident that lsandthebooks does.

And so your assertion, as I understand it, is that every J.S. whose actions took the form of a letter or telegram was actually a single person?