This event happened roughly two years before the start of the comic/novel.
Hessa, three years prior to this event, had managed to get the local Small Business Association to give her a $25,000 loan to open up a bar. Hessa had scouted the perfect place; a lebanese resteraunt that had failed about a year prior. It took her about a year of perparation and planning, but the space remained vacant the entire time.
She secured a decent lease with the owner and invested most of her loan into the build out. Unfortunately, she ran out of money, and she couldn't get a loan without puttin up some sort of collateral, which she didn't have. Well, the landlord offered to find whatever she needed, on the condition he got a 10% ownership in the business and she repaid him with a rather steap interest rate.
Hessa knew the deal was bad, but she took it anyway, knowing her business would be a success. And it was; she was able to make significant headway in paying back what she owed him, for the first year or so. However, incidents started happening that cost money, such as vandalism, equipment failure, costly repairs. Suddenly bills were piling up and she was falling behind on her loan payments.
He offers her complete forgiveness on her loan for a 50% ownership. She refuses. Instead, Linore uses some of her savings to buy a 20% ownership in the business, and starts hanging around more to prevent the vandalism. The cash infusion helps and Hessa is able to return to making payments on time, despite several close calls and 'almost expensive' mishaps that Linore prevented.
Hessa's landlord informs her that he's got another tenant willing to pay twice what she is for the location. He says that, despite being an 'owner' in the business, he's thinking about evicting her. After all, he's invested heavily in the business and has yet to make any money. So either she pays off her loan immediately, or she has 60 days to vacate.
Hessa talks to Linore, but by this point neither of them have any money to speak of; all of their personal savings are tied up in Ignite. No one will even return Hessa's phone calls about a loan; Linore finds out the land lord is definitely strong-arming loan officers and threatening them, however, since it's not a magical related offense the Enclave won't get involved, and the police say there's not enough evidence to make a move on him.
Things come to a head when the land lord sues Hessa for a majority ownership of the business. His argument is that given how much money Hessa owes him, a minority owner, he should be allowed to forgive that debt for an equivalent ownership. He has slick accountants who are able to make all of this seem perfectly reasonable. Hessa can't even find someone to represent her, and instead stays up for nights learning the relevant laws and how to file motions in civil court.
It's at this time that Simon learns about the situation with Ignite. He's not very interested in it at the time, but the land lord was a client of his (bought information and magical items), so Simon half listened, thinking that the "poor Charon sisters were being completely fucked by this ape of a man".
Hessa askes to meet with the Land Lord at his offices. She's nervous, but she had a plan. When the meet, she makes it clear that she's willing to trade sexual favors for at least some loan forgiveness. He says he'd have to see just how good she is; she can afford to give him a sample of what she's offering, can't she? She agrees (that was her plan, after all) and he locks the office door, telling his people he doesn't want to be disturbed. She immediately uses her dominate ability on him, and forces him to say on a phone recording that he's just using the lawsuite to try to force her into sleeping with him, and what's more, he's been blackmailing people to make sure she can't get loans. The entire lawsuite is a shame, as far as he's concerned; he has no interest in the business.
As soon as he says this "parade of horribles" on a recording, Hessa releases him, makes him fall asleep and then tries to use the recording in court. Unfortunately, none of what the land lord said had any bearing on the suite and so the judge dismissed the recording.
Unfortunately for Hessa, the land lord put two and two together, and realized she had some sort of magical ability to dominate him. So, he contacts Simon, looking for something to protect him from that kind of ability. Simon sells him an item that, while it won't fully protect him, will allow him to know if someone is starting to use that on him and should allow him to break free, if he's mentally strong enough. The land lord assumes he is and spends more than what Hessa owed to aquire this protection.
The land lord then declares his intention to 'own' Hessa, and use her abilities for his own gains.
What Simon didn't tell the land lord was that he was now intending on learning more about Hessa. He started showing up to Ignite, sometimes watching Hessa's shows, other times simply drinking alone, with a book. Ever time he made sure to catch the eye of either Hessa or Linore, knowing that he would need them to believe he was just a new patron when he made his move.
For Simon's part, he believed Hessa's abilities were dangerous and needed to be controlled. She needed some combination of protection, guidance, and managing. His intention was to make sure he had control over those abilities, or those abilities were somehow neutralized. (He often remarks to Hessa that there was a version of this where he just murdered her and moved on. She always laughs and tells him she's glad he didn't.)
During one of her performances, the land lord shows up, and in the middle of it demands they discuss all the money she owes him, among other things. Embarassed, Hessa rushes him to a back room where he can be heard yelling his demands.
Linore stands outside the door, clearly worried, but not entering. Simon approaches her and asks what's going on. Linore tries to brush him off, but he tells her that he might be able to help. He has an accounting certification and runs several very profitable businesses; he might be able to put her in contact with his own loan officers if nothing else. There's no reason a business as profitable as this one seemed to be should be unable to get a loan.
Linore confides in Simon about the lawsuit, though it seems clear to him that she knows nothing about the recording or how Hessa got it. Which means the Enclave Guardian knows nothing about her sister's true abilities. He found that fascinating, but also encouraging. It meant she didn't use it obvious enough for her sister to notice it.
Suddenly, there's a loud crash, and the Land Lord comes screaming out of the room, badly burned. Hessa is standing in the middle of the room, as papers and furniture are engulfed in flames, staring at him like she wanted to kill him. It lasted a moment, before her eyes met Linore, and the flames immediately extinguish, and she collapses.
Police are called and Hessa's arrested. It seems clear she attacked him, with Magic which is an incredibly serious crime. She could be looking at assualt with a deadly weapon, or even attempted manslaughter.
Simon contacts Linore and tells her he knows someone on the police force. He can make sure that all the facts reach them about the land lord and the shady loan practices. It should at least help provide context. He also offers to help pay for a lawyer. Linore thanks him, but tells him not to do anything. She appreciated his kindness, but she would solve this herself.
Meanwhile, Simon contacts Miranda, informing her of the entire situation, including what the man was actually after. He then informs her of the recording, suggesting rather strongly that Hessa's phone be too damaged to recover much, save for a partial recording. Miranda fakes the evidence flawlessly, and is able to use it as evidence to get Hessa released pending arraignment.
After Hessa is released, Simon introduces himself. He meets with both Linore and Hessa and explains that he's done some digging and it seems like this land lord is quite shady, and probably trying to strong arm one or both of the sisters. He says that his contact in the police force told him they found a recording on what was left of Hessa's phone where the land lord claimed he was trying to force Hessa into sleeping with him, and that's what all this lawsuit stuff was about.
Linore looses her shit, wanting to hurt the guy, and Hessa just rolls with it. Finally, Simon askes Hessa if they can talk alone, he has some financial questions; he thinks he can help. She agrees and as soon as they're alone, Simon admits he knows the real reason she lost her cool. He tells her that, until the moment that she attacked him with fire instead of her other abilities, he was planning on simply getting the land lord out of the way and finding a way to control her himself. But he now had seen who she really was, and there was no danger. In stead, he wanted to help her get out of this mess, and ensure no one is ever able to try and use her or her abilities again.
Hessa is beside herself, but she takes Simon at his word. She doesn't like the how and why he's involved, but they both agree Linore shouldn't know details. Because the lawsuit has a copy of the recording on record, it could be inconvienent if someone were to notice that existed. So, Simon proposes Hessa go to his bank and take out a loan for the full amount owed. Simon will cosign, on the condition she also hire him as her accountant, and take his advice. She agrees. She then files notice of her ability to pay the amount in full, the court orders her to do so, she does and the case is dropped.
The next day the city's court system crashes and several cases had motions, evidence and the like deleted as a result. This includes Hessa's recording. Simon marvels at how easy it is to hire an anonymous hacker. Or how easy it is to make the contract magically binding, even over the internet. The hacker will never be able to devulge information about the hack, or they will instantly die.
Simon informs Hessa that his next step is to kill the land lord, and make it look like the man has disapeared. It's the only way to make sure no one finds out about her abilities, and the man clearly deserves it. She's resistant, but Simon explains that this isn't the kind of man who backs down. It will come to an altercation one way or another, at least this way Simon can control the situation.
Hessa relents, on one condition. She's there when it happens. Simon agrees. Later that night, Simon meets the land lord one on one. The man realizes he's been set up when Hessa appears, but Simon unleashes his dark magic and not just murders the man, but tortures him a bit. Hessa watches, horrified, but unwilling to look away. Eventually, Simon fakes up a will leaving the building to Hessa, and then stages the room as if a magical deal went sideways, and he ended up dead. He made sure the evidence all pointed to a dark magic user, and then they left.
The next day, Linore told them both that the land lord had been killed in an illegal magic deal gone wrong. She recused herself from the case, considering, but she was glad he got what was coming to him. Hessa informed Linore of how Simon helped her get the loan and how he would be their accountant, now. A week or so later, Hessa was informed about the building being left to her in the will, and all the paperwork was signed.
Hessa and Simon have a deeper understanding for each other because of this. Somewhere along the way a friendship developed and he's quite fond of her.
Linore also fell for Simon, in her own way. He never asked for anything unreasonable, always wanted to minimal in return for what he gave, and most importantly respected and fought for her sister. She felt like she trusted him. In the two years afterwards, she felt herself grow close to him.
Miranda knows of Hessa's power, but at the time she had no intention of ever interacting with Hessa, so it didn't matter. This was a favor she did for Simon, because of a debt she owed him, and what he was asking for was the right thing to do. She doesn't know he was involved in the murder of the land lord, however.