Hi, Parker. If you have screenshots where he asked you to pay him outside Italki and about the cancellations as well, please send them to the Italki team. I don´t know if you can get your money back, but you should definitely contact the support team and tell them about that. He wants you to pay him outside Italki because this way Italki won't take any comission from him, and this way he can keep all the money for himself.
Anyway, keep in mind that after each lesson you receive an email from Italki. You can mark the lesson as complete and give feedback, or you can ignore the email and after 3 days the lesson will be automatically marked as completed. When you receive this email you have the opportunity to click on "there was the problem with this lesson" and inform Italki about the problem. Once a lesson is marked as completed, by you or by the system, you have less chanches of receiving your money back, but, who knows? Email Italki right away.