Thanks for the awesome feedback!! I will be trying to post a new version tonight; there have been some updates which I think will at least partially address your confusion. Let's see if I can break things down a bit now though for everyon'e sanity:

Okay, finally got time to take a look again. So, here it is:

Bearings: It might be worth adding "Any time a rule says that you get to bear something, it becomes a bearing on your sheet."

I was hoping people could infer that, but yeah I'll go over how I use the language of bearing to make sure it's clear.

Presence: What is this used for again?

It's a concept. If you are present you can be affected. If you are not present you can't be affected.

Paradoxes: How do they occur? It it purely a MI tool, or are there rules for it?

Full mechanics in the new version coming up. :)

Discern Realities:
I thought that you had to roll the last bearing that you've added, but from the example it seems you get to roll the last bearing you've rolled?

Yes, the last bearing.

? Gain a bearing on something here. The MI will give you tags; add them.
So the MI gets to decide your bearings? That somehow seems wrong, unless bearings are supposed to be something that the player does not have complete control over. Or do you mean "Choose something here to gain a bearing on."? So you might not decide the exact tags, but you still decide whether its a bear or a flower pot that grants you your new bearings.

You decide the bearing, the MI then provides tags for it. Some tags can be assumed. If you add fire to your bearings it will probably have tags designating harm. The MI may add other tags though, especially depending on the result, such as trauma.

Staring into Infinity: Except for very weird cases, won't you lowest bearing not always be -1 (I.E. the innermost ring)?

It's been revised in the latest version to work the opposite way of staring into the Void; you look at the innermost incomplete circle and count the filled cells, then from that you figure out the modifier.

? Describe some thing not here and gain a bearing on it. The MI will give you tags; add them.
Okay, now I'm confused again. Are the tags bearings that you should add to your sheet? Or are they something else.
On a separate note, Staring into Infinity seems like a free pass (as long as you roll high enough) to gain a bearing on literally anything. Is this true?

Yup! You can gain a bearing on anything. I may change it to instead give +1 forward to doing something with that.

Staring beyond into the Void: "Count the empty spaces as if they were bearings going outward." I have no idea what that means. The example didn't really help. I'm also guessing that whatever number you end up with is what you should roll with? That isn't explicitly stated.

There is a visual example in the latest version. Hope it helps!

I'm also a bit unsure how the move helps "Avoid erasure or trauma" in the fiction. It only works for weird trauma, like in the play example?

It's been revised a bit. Now it's just "Avoid trauma." In the fiction, it is very much intended as one of the ways for ending the escalation of trauma. The other is to get the hell out via shifting realities. It's somewhat like holding steady from Monsterhearts; you ground yourself by looking past all the noise, at how everything is just paint on the empty canvas of the Void.

Conjure up something:
Is there are reason why the MC should be the stewart of Monuments and Whispers, instead of the "owning" player? It adds extra complexity, and I don't immediately see any huge benefits from it.

The MI needs to add it to their own sheets, especially because threatening monuments and whispers is a thing they do. Otherwise there's no stewarding, they are just on the table.

Erasure of harm: Isn't erasure a bad thing that is connected to paradox? Does this mean that the character that caused the harm suffers paradox, and thus possible erasure?

Erasure is not necessarily a bad thing. Erasing trauma or harm or undesired tethers can be a strategy. Whether paradox occurs is up to whether both players are present, press it and succeed their rolls. If it's an NPC, it's up the MI. After paradox resolution, the losing player will experience erasure of a bearing.

"She adds the Soviet Gulag above her hillbilly hometown." Okay, so it might finally have clicked for me. Bearings describe your reality? So when she got the Soviet Gulag bearing, it became part of her reality? Because that is a very different (and cool) multi-world setting than what I imagined. Or.. maybe not, given the ending. Now I'm just confused again.

Bearings don't represent your reality. They represent your consciousness, what is important to you, what you have a connection with, what you are aware of. When she gained a bearing of the Soviet Gulag, she is able to distinguish it within the infinite realities within all Infinity. She can shift realities to the Soviet Gulag. Or she could also converge the Soviet Gulag with whatever reality she's in. Haven't really elaborated on that possibility. :) But no, it's not "part of her reality". Her reality is wherever she is present. Think alternate universes.

? To roll plus a bearing, take the highest modifier reached within the bearing’s direction on the map.
I think this needs to be specified when bearings first get explained, because it is kinda crucial. Probably highlight it more in the example (it seems like you keep rolling for the outermost bearings, never for bearings further in with the outermost modifier). Having a notebook and a diary in the same bearing doesn't help the clarity of the example either. Swap the diary for something else, put the tether on the notebook, and explain why she gets to roll +2 with the notebook.

Good points, it's a bit confusing.
 

I haven't read playbooks, since I think the base rules need to be sorted out before I look at that.

Yeah, a lot has been worked out since I made the playbooks, so I want to revisit them myself.

Thanks for the reply! It's helped me realize a few things I haven't been clear about.

I think the most immediate thing to address would be your concerns about realities being too ephemeral. I'm going to update the MI's principles to include "No reality exists in isolation." It's within the MC's moves to cross paths of the Outsiders -- and not just player Outsiders but NPC Outsiders as well. Another point is that your secret bearings will be able to be read using Look Into Infinity. Also, tethers/anchors will definitely not be static especially if the anchors are people who hold whispers and/or are in PC-NPC-PC triangles and/or are looking after your monuments and/or become Outsiders themselves.

The conflict is totally in asserting realities and it definitely won't be just a snap of the fingers. I haven't clarified the rules for erasure. Sorry!

Regarding bearing knowledge, yes you get a new bearing. You don't need to fill the entire innermost circle. You can and should fill in spaces outward as well. No rules except you can't fill in spaces sideways where there would be gaps underneath, and I may say no going past +2 during character creation.

Anyway I'll definitely be updating with examples. Thanks!!