Dess even picked up Wisdom.

This is practically a key moment. If Biobob hadn't given Wisdom in the Pandora's Box, the viability of this type of playthrough would have been reduced to zero.

Added 12 minutes later
But the alternative option is much more interesting. It fundamentally changes the ideology of completing the map and significantly increases the speed of completion (at least by a week compared to Dandy). If, of course, it is feasible.

The main idea is that, without giving Armageddon at the end of the first week, allow the blue player to open the quest pillar before the Dungeon with a hero with damage and other stats. And after opening the brown tent, manage to free the hero from that dungeon. Then, Metataxar and wings will simply not be needed anymore.