Watchdog: Passing a string of an expanded user (Pathlib) into observer.schedule gives Illegal Instruction 4

As per the title, the commented out code works, while using Pathlib gives me an Illegal Instruction 4. Printing the paths to terminal shows they're set correctly, and commenting out the observer.schedule line runs the program with no errors.

class ObserverLoop:
    def __init__(self):
        self.folder = Path("~/Desktop")
        print(self.folder.expanduser())
        # self.working_path = os.path.abspath(os.path.expanduser("~/" + "/Desktop/"))
        self.working_path = self.folder.expanduser()
        print(self.working_path)
        self.event_handler = MonitorFolderChanges(self.working_path)

    def start_loop(self):
        tf.key = secrets.api_key
        observer = Observer()

        observer.schedule(self.event_handler, self.working_path, recursive=False)
        observer.start()

        try:
            while observer.is_alive():
                observer.join(1)
        except KeyboardInterrupt:
            observer.stop()

        observer.join()