Walkthroughs for custom maps.

I don't see any problems with the Dragon Cloak –
yes, first you need to get the Watchman's artifact from two Inferno castles – but any hero with intelligence can handle that.
There are 2 days (221+222) to get the Dragon Cloak and Boots of Levitation, and then you need one more hero to pick up the Boots of Levitation. True, by day 221, few will have enough movement points left, but 222 is still available to us:)

The lack of wisdom and, as a result, teleportation for Rusty is a drawback. But this guy has 4 damage dealers per turn, and the main thing is to get the quest item from him. And he reaches the quest item in approximately 2 days.

There is also a rather ambiguous point regarding Dessa. Almost everything depends on the timing of Rusty's release. There is a basic timing that cannot be abandoned – entering the Inferno of Earth on day 221 (because we need the bonus from the Legion statue) – although this statement can be disputed. If we have a timing of entering the Inferno of Earth on day 221, then Orrin with Logistics will definitely make it to Beertent on day 222, but there will be few movement points left. It needs to be checked whether Orrin will have enough movement points without Logistics to make it in time, but without tests, this is a potential weak point. The optimal solution would be to keep Dessa and have Logistics for Orrin. After all, the intermediate timings before day 221 are not so important.

Among the advantages of Rusty's prison, there are also an extra 2,000 sapphires for our army (we don't even consider minor things like Titans), which, although not much, will help in the next battles :) And we still have the Armageddon Blade, which will help in battles before Rusty. And then, a small army from the prisons (except for the last two) will be added to the area with Operator – well, it's a small thing, but it's nice :) – because then you won't have to chase these heroes. The Operator himself, as well as the last two heroes, should be left for Dameleon.

in general, according to approximate timing estimates:
222 – Rusty
223 – quest item, release of the red prisons from the Operator's zone, collection of the remaining quest items. And, most likely, the game will be completed :) Well, maybe one or two days will be lost somewhere. But in any case, at least 2 weeks will be cut off from my record.

So, potentially, the speedrun will be much less time-consuming – not only compared to my struggles, but also compared to a normal playthrough.

Honestly, I'm puzzled as to why Nasos lost motivation to implement such a great idea.

Added 32 minutes ago

One consideration that could ruin the plan. Can the blue player hide one of his heroes in the castle garrison when Carrot Pit approaches the prison?

Well, the red player, for example, is in this position throughout the game and does not place heroes in the garrison. I doubt that the blue player has more advanced intelligence :)