This might just be me, but I feel like alot of people are missing some key aspects of Alastor's lore dump in the recent episodes (3and4). Ignoring the fact that Rosie is his owner, a character reveal that I think is just completely perfect for her, we are also shown that Alastor is completely petrified of being vulnerable even to himself.
What do I mean by that? Alastor is a man that lived in the peak of racist America as a visibly african-american man. He is incredibly prideful, and he did not get his radio-host position by having true friends. While I love the fanon idea that he killed for the sake of others as some kind of vigilante, that is simply not in any way confirmed in cannon. We do not even know if he had a relationship with any of his parents. To the people around him in the business, he is simply a pice of prized meat that they can take a bite of and discard like trash. We see that in the way all of the white people around him treat him, to the point that they are completely fine with unapologetically ruin his clothes without even acknowledging him, even doing it again because its funny.
For a prideful man like Alastor, is there any surprise that he would try to claim any power he can for himself? Even if that power comes in the form of murder? But the power high of murder is not enough, he needs more, both in life and in death. His ego could not take loosing that high.
We know that Alastor is a spiritual man, he has to be in order to even try to summon a demon. I have no doubt that Alastor would never outright sell his soul, I do not think most would. He knew he would go to hell, but he does not know anything about hell. How would he even gain power there, and can he bear the thought of being weak while gaining it? We already know the answer tho that, he cant. His sense of self can not take it, he can not be vulnerable.
He is willing however to sell his services, and his service better than any other of course. And if his soul is being held as collateral until his service is fulfilled? Then so be it. It is not the first time he has played on someone's else strings to get what he wants after all. It is not like his soul is gone forever, and for the price of more power than he could ever imagine?
However, the terms of his contract is vague. At the time of Alastor selling his service soul, Alastor was so prideful he didn't bother to question why Rosie was willing to give him all of this power, what was so special about him. Why couldn't she make someone else do whatever service she needs him to do, what even is she seeking? Is it even possible for him to ever finish this service? Is he eternally forced to go on a wild goose chase for the price of his power and ego?
In the beginning, Alastor must have seen this power as good as his. We know this because he calls it his own when he spends time with Vox (Vincent is such a perfect name for him). It does not matter that he has not fulfilled his contract yet, because he will. He has no doubts that he can do it after all. But it's not his power, it's Rosie's, and at some level he has to acknowledge that.
And lets talk about Rosie for a second. We know she died in the 1800-ish, even earlier perhaps. She is not above modernising her territory after all. The way she presents herself to Charlie, to everyone really, is that she is the friendly listening ear in the neighbourhood. She might not be able to do anything, but she has connections, and she is your friend. She can be your best friend even, so just tell her your woes. Tell her everything that weights your heart, and your best friend Rosie is willing to help you! She will move heaven and earth for you if she can, but even her generosity has to end. But at some point, you have to pay a price. And your friend would never hurt you, so you can trust that she can take care of something as important as favour involved with your soul. And if you cant fulfil your side of the favour? Your soul is as good as hers now.
Now, let's look at Alastor by the time he has befriended Vox. He is no longer as ignorant of how Rosie works, and has had nothing in his life that challenges how real friendship works. You cant have friends when everyone around you is connected to your owner, or wants something from you. So when Vox suggested a partnership solidified in friendship? Alastor can not believe he has allowed himself to become this vulnerable, that Vox, someone he enjoys spending time with (and maybe even respects a little), would allow himself to be so vulnerable. Friendship does not exist, especially for people in hell. So Alastor decided to cut him out of his life.
It is in this interaction, that we observe just how scared Alastor is of being vulnerable. Because if he is vulnerable, then someone may take advantage of him again. He may even think that he did Vox a favour.
But just because Alastor does not want an emotional connection with someone, does not mean he does not make them. Just not as long as it is not in the pretence of kindness, where he is vulnerable. We can see that with Nifty. Alastor genuinely cares about Nifty (he even still has the roach crown), but he would never allow himself that without owning her soul.
Modern Alastor, is not blind to this weakness. At this point, he is painfully aware just how conditional Rosies power is, an how far away it is from it becoming his own. At this point, he is barely even maintaining the illusion of his power to others, let alone to himself. He is starting to question if there even really is a light at the end of the tunnel. How long is she going to string him around? And can he get his soul back if he gave up this power? Can he live with himself being powerless?
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