For this to be possible, combine the season 1 Cave of Sighs, the Crypt (I'll use this upper starting room as an example), the Troubled Bridge, and Olmec's lowering gate. Make it impossible to get into the Crypt via Cave of Sighs and when it comes to Olmec's gate, just have Kirk say "Olmec's gate won't lower for some reason. It must be old and rusty, so you'll have to take the Cave of Sighs in order to grab the item. I'm sure it will open if you grab it." Also make it impossible to get into the center room via The Pit and via room below it. The only way to grab the item is to use the Troubled Bridge-Crypt door.
What do you think of this idea for a Legends temple run if season 4 ever comes to us? I think this could be possible.