Alastor & Lilith are connected.
Husk: "You've been gone a while and it's not like anybody knows why."
Alastor: "They don't need to know."
For a while now I've had some thoughts in regards to Alastor and Lilith's deal, and it involves much more than their mutual 7 year absence. We've already covered Zestial's comment about Alastor falling to Holy arms while Lilith is indeed in Holy lands, and obviously Lilith is the #1 suspect as to who exactly owns Alastor's soul, but I am suggesting that their connection may be much deeper than that.
As a disclaimer, I must warn you that I took Amir's comment about Alastor's sexuality as a greenlight, since his aromanticism is supposedly no longer canon (and much more from the pilot era is no longer canon). If you're interested in this crazy theory, I hope you'll stick around for the evidence I collected.
Faustisse's Painting of Lilith
Faustisse, although no longer working on Hazbin, provided a lot of beautiful art to promote the show, and this piece is featured in the pilot. According to some sleuths online, Faustisse confirmed the hands in Lilith's hair and unzipping her dress are in fact Alastor's. Upon further inspection, I noticed the lipstick marks on her back are also drawn in such a way that they look like Alastor's signature smile, and the snake dress has his stitched smile pattern. This was the first piece of early foreshadowing concerning their involvement.
During Alastor's reprise, the jackpot suggests 3 apples represent the Morningstar family (Charlie, Lilith, Lucifer). However, one of the apples is replaced by a skull with deer antlers. I believe this is implying Alastor wants to replace someone in the family with himself.
It's an interesting approach when you remember this scene moments before. Alastor looks at Charlie/Lucifer, turns his head to the left where Lilith is, looks her up, down, and then smiles.
Lucifer is the King of Hell, estranged husband of Lilith, and father to Charlie. Niffty dubbing Alastor 'King Roach' is foreshadowing his plan to replace Lucifer. When you remember Alastor's immediate dislike and 'forced' rivalry with Lucifer in episode 5, as well as his out-of-nowhere idea that he is a father figure to Charlie, it suddenly makes sense if he has reason to act that way. Step dad angle, perhaps? Why else would he have such animosity toward Lucifer, to the point his eye began twitching in anger, unless Lilith had perhaps informed him of Lucifer's absence in Charlie's life?
I noticed in Alastor's prequel comic he has a panel with something similar visually, in which he is angled beneath a rose bush. This could be a bit of a stretch, but three roses on a wreath is well known to have a romantic meaning behind it.
Re-reading the comic, I was surprised to see hearts around Alastor as he hummed along to a song.
Leaving the comic behind, there is another clue in episode 5 which suggests their involvement.
On the left is Lucifer's duck with his top hat, sat alone on the shelf above a suspicious looking box. On the right, a painting of a feminine looking duck with ram horns, similar to Lilith's ram horns. Beneath the Lilith duck is another duck with deer antlers. I believe this is subtle foreshadowing as to where Lilith and Alastor have both been for 7 years.
Lilith Asked Alastor to Mentor Charlie
Alastor has been trusted with the role of Charlie's mentor. I believe Lilith wants Charlie to become Queen of Hell. In episode 1, Charlie implies her belief in sinners' redemption is thanks to her mother, and that she wants to make Lilith proud. Lilith lead the uprising and resistance movement, but currently is in Heaven for mysterious reasons. Alastor is the Queen's Hand doing her work where Lucifer has not.
Alastor & Lilith parallels
• Both sinner demons who were once humans
• Lilith wanted to reshape Hell, suggesting she is a rebellious character with a moral code
• Alastor was a vigilante killer who culled people he considered bad, suggesting he is a rebellious character with a moral code
• Alastor was titled as the King of Spades in Husk's deck, while Lilith is positioned as the Queen of Spades
• Both broadcast throughout Hell
It's very likely Alastor wants the position as King of Hell for selfish reasons, as we know he wants out of his deal. That deal is most likely related to the hotel, and Alastor is slowly becoming fond of the gang, which is disrupting his plans. However, the connections between him and Lilith are quite striking, and I thought it was telling that Lilith and Lucifer are not only split up, but episode 8 implied Lucifer had slept with Eve! I'm wondering if this was infidelity, and if so, was that the reason Lilith sought out another man?
The possibilities are endless as of now.