So we know Alastor and Lilith disappeared at the same time 7 years ago. And we know that Lucifer had a meeting with Heaven which began the exterminations. We don't know when that happened though. Either they're not mentioning when the exterminations started because they've always happened or because revealing when they started would give too much away and make it too easy to guess things. All Charlie knows is that Lucifer went to the meeting and she assumes he gave the go ahead for exterminations. But the exterminations haven't always happened. They only started after the angels, or specifically Sera I think considering no other angels knew about it, became afraid of the power and influence Lilith had over the demons.

My current theory is that that meeting was called between Sera, Adam, and Lucifer because Alastor and Lilith were planning on working together with him broadcasting her voice on his radio station to inspire the other demons to rise to war against the angels. I think Sera demanded that Lilith and Alastor be separated with Lilith making a deal with Adam to stay in heaven where she can't empower any other demons with her voice or even contact anyone in hell and that Sera demanded the exterminations happen as well in order to not only lessen the demons' power but also instill fear in them in an attempt to prevent future uprisings. I think Alastor was given the options of either be killed or sign a contract limiting his power and requiring him to stay away for a while so that their little idea of rebellion is forgotten amongst the masses. I especially think that because of Zestial's comment about folks thinking Alastor had fallen to holy arms. Maybe Sera is his contract holder. That or they tried to straight up kill him and he somehow escaped barely alive and it's taken this long for him to heal and regain enough power for him to feel comfortable revealing himself to society. But trying to kill him wouldn't explain the contact or his need to 'unclip his wings'.

Apparently there's another Alastor theory going around! It's Roo who is in control of him, she's the Root of all Evil or something? I too, have this deer man spinning in my head microwaving so I am eating up all these theories

I do not know much of this Roo character, but with all the eyes always watching him in the background it would somewhat make sense!

ohhHHHHH

I'm ngl I had no idea this character was even a thing and had to look it up in the wiki and hOLY SHIT.

That would... honestly explain a lot.

I still do think that Lilith being gone for the exact same timeframe as Alastor is a bit too specific to be complete coincidence, but maybe it doesn't have anything to do with Alastor's deal after all? I've been struggling to try and pinpoint a motive or purpose for such a deal, so maybe neither Lilith nor Eve are actually the answer here, or only a part of it?

I'm still in the process of rewatching the season and collecting notes on the side to hopefully try and make sense of later on, but knowing this character may come into play in the future definitely adjusted my perspective on things...

Like... Alastor seems to absolutely despise the idea of being seen as altruistic and selfless - maybe his overarching goal and/or his end of the deal is to spread as much evil and carnage as possible or sth like that? Idk man.

He also keeps everyone around him at a very deliberate distance (unless he's got an agenda and uses the friendship angle and physical contact to manipulate), then he seems almost genuinely sentimental during his talk with Niffty? But imo it sounds like he's expressing wishful thinking more than anything.

I think he's deliberately trying not to get attached to the hotel and its inhabitants because he already knows it's not going to stay that way, since the plan seems to have always been that the hotel and, in extension, Charlie, are mere stepping stones to whatever unseen goal he has. For now we are meant to assume that it's an elaborate plan to free himself from whatever contract it is that's plaguing him, but I think there's a lot more to it than that.

What I'm currently trying to figure out is what his plans are for after that...?

Like... what is he going to do with the newly regained freedom? What was the deal keeping him from doing?

Maybe it'll have near apocalyptic consequences and he was restricted for a damn good reason :'DD either way I'm fucking terrified.