@timeisrestored
I agree the October-June timeline is the biggest question mark, but I don't think we're ever getting answers about what exactly went down in that period... Gio wasn't privy to whatever discussions were happening between Bambosh/Hussie/Miles/lawyers due to NDA's, and none of those parties can release that info, or really have any incentive to. Bambosh might I guess, but they seem to have pretty firmly washed their hands of the whole situation, and also I'm sure does not want to get sued.
My 2 cents, whatever they're worth, is that it really is down to Hanlon's razor -- it was incompetence, from both ends, not malice from either. I will be putting on my speculation hat below -- I am not asserting anything happened that isn't directly confirmed by Gio/Miles' statements.
The Timeline, as presented by Gio:
October 2023 -- Miles first approaches Gio/Bambosh, Gio has reservations, Miles says do not worry about that stuff (potentially, and, imo, probably, without consulting a laywer). Bambosh signs an NDA that Gio/Bambosh are both happy with, with the expectation that Gio will be sent one after. Multiple people are on vacation after this so not much happens for a month.
Side note: I think it is crazy that contract negotiations like this are taking place over whats basically IRC... it's surreal to see Miles drop stuff like the Cease and Desist threat with the hawaiian rocket power guy as his avatar. Maybe I'm out of touch but it seems a wildly unprofessional medium to have those kinds of conversations. Whatever! Useless tangent!
November 2023 -- Bambosh is sent a license of some kind to look over, and gets their own lawyer involved.
Hanlon razor/wild speculation point number one -- it is entirely possible that Bambosh ended up with a lawyer that wasn't very good at their job and/or was just not making Bambosh a priority. I don't have a contract laywer on retainer, nor do I assume most normal private citizens do, and if I were getting one to look over some documents that I thought were relatively innocuous I probably would not be shelling out a bunch of money. I think this primarily because of Miles comments about the lawyer ghosting them and not responding in a timely fashion -- Miles reads that as an intentional delaying tactic, i.e., malicious, I read it as (there are other, higher priority cases in that lawyers load or the situation has not changed and there's no point reiterating something that has already been stated).
This is, again, wild speculation, but Miles intimates that they don't even have a lawyer... I think the tone of Miles' messages suggests he thinks the "lawyer" is just Gio, at this stage, but we really have no idea.
Hanlon razor/wild speculation point number two -- at some point in here, Miles/Andrew talk to their own lawyer, and are told that Gio's involvement is a bad idea or straight up a non-starter. Gio reads the flip-flopping on this point as intentional manipulation but I think it's just incompetence -- Miles or Andrew promised it wouldn't be a big deal, lawyer says actually it would be a big deal, now it's a big deal. Which is, again, why having contract negotiations over discord is ridiculous, but whatever.
Hanlon razor/wild speculation point number three -- I think the really big point here, and if I were trying to construct this post intelligently I probably would have lead with this, is that Hussie/Miles don't think whatever co-ownership deal Bambosh/Gio have set up actually holds water, legally speaking. The impasse, from Gio's POV, is that Bambosh can't sign it without Gio's involvement, they refuse to send Gio the NDA, so nothing can happen. That behavior makes no sense from Hussie/Miles POV, and Gio sees it as malice... but if whatever lawyer they have takes a look at it, says "nah this is not legally binding, you don't need this guy around to move forward" then it makes sense to get Bambosh to sign off on things without having to put someone they do not want involved under contract. In terms of incompetence v. malice, they fully intend to involve Gio in some capacity after Bambosh signs the license... they aren't lying, but it's a sticking point.
That explains messages like "as for your involvement, running the project as a twosome, we get it and as im just now getting back we can look into getting you under NDA so you can mutually look over the license." Gio reads this as a lie, more or less, but to me it scans more like "Bambosh can sign this without you, but since it is a sticking point for the both of you, we will continue to look at getting you involved [although our lawyers have already told us not to do this for whatever reason]"
November-February
Firmly in speculation territory here. We have no idea what happens, and at least officially, nor does Gio. We get a conversation with James Roach that says "I’m assuming you’re not familiar with the details then but right now from what I’ve been told things are locked up with lawyers for some reason"
Couple of assumptions here -- totally possible Gio is more in the loop than they claim and simply cannot fess up to it because it would have involved Bambosh breaking NDA. It certainly seems like Miles thinks this is the case, as the big message in May addresses both of them as a unit despite Gio claiming pretty much complete uninvolvement for the remaining months. Regardless of whether or not it's true, it explains the hostility Bambosh claims to have experienced -- they believed Gio was using them as a proxy, which is why Miles speaks of Bambosh kindly in the message that started this whole thread.
Other assumption -- not much happens in this period because it was primarily over the holiday season, and, again, Bambosh got a lawyer that was not treating this as a high priority for whatever reason. Miles and Andrew both had vacations in October, sent things in November, look things over, maybe exchange emails requesting clarification or rewording or whatever... I can very easily see how things proceed cordially till February with bi-weekly email exchanges. Or, as Miles suggests, maybe Bambosh didn't even have a lawyer in November, and was either looking things over on their own or spent some time shopping for one in this period of time.
February-May
We have literally no idea what happens here. Things obviously stop being cordial at some point.
My interpretation: Bambosh continues to assert that they won't sign without Gio's involvement, using an actual lawyer. Probably more prevarication over wording. Hussie/Miles/lawyer assert, Gio can be involved but will not until the license has been signed and despite whatever Gio thinks, this is legally possible. If Bambosh does not sign a license, the C&D will be issued at some point.
It stretches out for a long time, because, despite what Gio asserts, this was not a chess game on the part of Miles/Hussie -- they have genuine good intentions, do not see the license as a power-grab, and do not actually want to issue a C&D. They will use it, but it's more of a last resort than a bludgeon.
Privately, Hussie/Miles think that Gio is using Bambosh as a proxy and stonewalling to do... something, which is why they feel the C&D becomes necessary. I'm still very ??? about this -- Miles message in May (that's fun!) asserts they were stonewalling to gain some kind of leverage, and sort-of-says that leverage is weaponizing community against Homestuck if they are forced to issue a C&D, which makes very little sense. It's the best read I can get from the what we have, and this is one of those things where with extra context, "leverage" was a licensing fee or something and Gio/Bambosh come out looking a bit worse.
That really, really got away from me, and I appreciate it if you read the whole thing.