Just me thinking out loud...Let's say he asked Charli to meet with him so he could give her the money he owed her. Let's say he then planned a robbery to get that money back. Enter accomplice here. He did ask for money for tires that we've read he never got. He gives her that money, but plans on getting it right back. Now this I can see being totally planned out. He could have told her the money is down Hana or so and so has it down Hana. A good amount of money that she probably needed could be motivation for traveling with him. He's also had some robbery issues. I haven't gotten any farther but this could make sense. Robbery doesn't go quite as planned and she fights back or Nala gets in the way. hmmm
Or he could have been planning to get the money from one of his, um, customers in Keanae.